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[ CAS No. 31680-08-7 ] {[proInfo.proName]}

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Chemical Structure| 31680-08-7
Chemical Structure| 31680-08-7
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Product Details of [ 31680-08-7 ]

CAS No. :31680-08-7 MDL No. :MFCD00126498
Formula : C8H7NO4 Boiling Point : No data available
Linear Structure Formula :- InChI Key :YTCRQCGRYCKYNO-UHFFFAOYSA-N
M.W : 181.15 Pubchem ID :700608
Synonyms :

Calculated chemistry of [ 31680-08-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.14
TPSA : 72.12 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.01
Log Po/w (XLOGP3) : 1.26
Log Po/w (WLOGP) : 1.42
Log Po/w (MLOGP) : 0.03
Log Po/w (SILICOS-IT) : -0.17
Consensus Log Po/w : 0.71

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.9
Solubility : 2.28 mg/ml ; 0.0126 mol/l
Class : Very soluble
Log S (Ali) : -2.37
Solubility : 0.767 mg/ml ; 0.00423 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.85
Solubility : 2.54 mg/ml ; 0.014 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.79

Safety of [ 31680-08-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 31680-08-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 31680-08-7 ]

[ 31680-08-7 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 123-11-5 ]
  • [ 31680-08-7 ]
YieldReaction ConditionsOperation in experiment
93% With sodium nitrate; In neat (no solvent); at 20℃; for 0.1h;Green chemistry; General procedure: A mixture of aromatic compound (1 mmol), sodium nitrate(1 mmol) and SO3H-functionalized magnetic core/shell nanocatalyst (0.1 mmol) was pulverized in a mortar at room temperature for an appropriate time. The reaction was monitored by thin-layer chromatography (TLC). After completion of the reaction, CH2Cl2 (5.0 mL) was then added to the mixture and filtered. Evaporation of the solvent followed by recrystallization or column chromatography on silicagel of the crude product gave the corresponding nitratedcompounds in good to excellent yields. The nanocatalyst was simply separated from the reaction mixture by using anexternal magnet, washed with methanol/diluted HCl solutionand then dried in an oven at 60 C. Before reusing the recycled catalyst, it was weighted in any cycle, and after that, it was reused in subsequent runs. Furthermore, fresh catalyst was added to reciprocate decreased mass loss, if it was considerable.
87% With sulfuric acid; nitric acid; at 0 - 20℃; for 1h; General procedure: Nitration reactions were performed according to the methodology described by Chorev et al. with minor modifications.1 A mixture of 5 mL concentrated sulfuric acid and 10 mmol of the corresponding benzaldehyde was cooled to 0 C under vigorous stirring. Then, 1.2 equiv. of nitric acid, previously dissolved in 1 mL concentrated sulfuric acid, was slowly added. After addition is completed, the reaction mixture was then warmed to room temperature and stirred for 1 additional hour. The crude was then poured into crushed ice, the solid product was recovered by filtration, washed with cold water and recrystallized from ethanol.
82.7% With ammonium nitrate; trifluoroacetic anhydride; at 0 - 20℃; for 7.25h; 4-Methoxy-benzaldehyde (1 g, 7.34 mmol) was added to a mixture of ammonium nitrate (0.58 g, 7.34 mmol) and trifluoroacetic anhydride (3.56 mL, 25.69 mmol), which was cooled to 0 C. The reaction mixture was stirred at 0 C for 15 min and then allowed to stir at room temperature for about 7 h. Ice was added and stirred for 30 min. The solid obtained was filtered, washed with cold water (3 x 5 mL) and dried. Yield: 1 .100 (82.70 %); 1 H NMR (DMSO-d6, 300 MHz): 5 9.93 (s, 1 H), 8.40 (d, 1 H), 8.17 (dd, 1 H), 7.55 (d, 1 H), 4.02 (s, 3H).
82% With nitric acid; at 20℃; for 8h; General procedure: 4-Methoxybenzaldehyde (6) (5.0 g, 36 mmol) was slowly added to nitric acid (70 %, 30 mL) at room temperature and the mixture was stirred at room temperature for a further 8 h. The reaction mixture was poured into ice water (400 mL). The resultant solid was collected by filtration, washed with cold water, and washed with aq NaOH to remove the acid formed from the reaction mixture and finally purified by column chromatography using ethylacetate/hexane to afford the product as light yellow solid (5.4 g, 82%): Rf = 0.4(EtOAc:Hex-50:50); 1H NMR (300 MHz, CDCl3): = 9.91 (s, 1H), 8.28 (d, J = 2.2 Hz, 1H), 8.04 (dd, J = 2.2, 9.0 Hz, 1H), 7.23 (d, J = 9.0, 1H), 4.07 ppm (s, 3H); MS (ESI) m/z: 328 [M+H]+.

  • 2
  • [ 141-82-2 ]
  • [ 31680-08-7 ]
  • [ 58435-22-6 ]
YieldReaction ConditionsOperation in experiment
86% With piperidine; pyridine; In ethanol; for 18h;Reflux; General procedure: A stirred suspension of the appropriate benzaldehyde (10mmol), malonic acid (1.15g, 11mmol), pyridine (0.4mL) and piperidine (1.2mL, 12mmol, 1.2 equiv.) in EtOH (30mL) was heated to reflux for 18h. The solvent was removed under reduced pressure, the residue diluted with water (10mL) and acidified with hydrochloric acid in water (1N solution). The yellow precipitate obtained was filtered, washed with cold water, and dried to furnish the desired product as a solid used without further purification for the next reaction.5.1.2.1 (E)-3-(4-Methoxy-3-nitrophenyl)acrylic acid (21g) Following general procedure A, starting from <strong>[31680-08-7]4-methoxy-3-nitrobenzaldehyde</strong>, compound 21g was obtained as a yellow solid. Yield: 86%, mp: 234-236C. 1H NMR (DMSO-d6) δ: 3.96 (s, 3H), 6.56 (d, J=16.0, 1H), 7.37 (d, J=8.8Hz, 1H), 7.55 (d, J=16.0, 1H), 7.98 (dd, J=8.8 and 2.0Hz, 1H), 8.23 (d, J=2.0Hz, 1H), 12.6 (bs, 1H). MS (ESI): [M+1]+=224.3
86% With piperidine; pyridine; In ethanol; for 18h;Reflux; General procedure: A stirred suspension of the appropriate benzaldehyde (10mmol), malonic acid (1.15g, 11mmol), pyridine (0.4mL) and piperidine (1.2mL, 12mmol, 1.2 equiv.) in EtOH (30mL) was heated to reflux for 18h. The solvent was removed under reduced pressure, the residue diluted with water (10mL) and acidified with hydrochloric acid in water (1N solution). The yellow precipitate obtained was filtered, washed with cold water, and dried to furnish the desired product as a solid used without further purification for the next reaction.5.1.2.1 (E)-3-(4-Methoxy-3-nitrophenyl)acrylic acid (21g) Following general procedure A, starting from <strong>[31680-08-7]4-methoxy-3-nitrobenzaldehyde</strong>, compound 21g was obtained as a yellow solid. Yield: 86%, mp: 234-236C. 1H NMR (DMSO-d6) δ: 3.96 (s, 3H), 6.56 (d, J=16.0, 1H), 7.37 (d, J=8.8Hz, 1H), 7.55 (d, J=16.0, 1H), 7.98 (dd, J=8.8 and 2.0Hz, 1H), 8.23 (d, J=2.0Hz, 1H), 12.6 (bs, 1H). MS (ESI): [M+1]+=224.3
  • 4
  • [ 1738-16-5 ]
  • [ 31680-08-7 ]
  • 4-(4-methoxy-3-nitrocinnamoyl)tropolone [ No CAS ]
  • 5
  • [ 951-82-6 ]
  • [ 31680-08-7 ]
  • [ 212262-55-0 ]
YieldReaction ConditionsOperation in experiment
45% General procedure: The compound 3,4,5-trimethoxyphenyl acetic acid (8a) (200 mg, 0.88 mmol) was dissolved in 10 mL of Ac2O, followed by addition of substituted aldehyde 9a (136 mg, 0.88 mmol) and Et3N (1 mL). The reaction mixture was heated at 140 C for 12 h. After cooling, the reaction mixture was acidified with 35% aq HCl. The reaction mixture was left overnight and the precipitated product was filtered. The precipitate was recrystallized from absolute ethanol afford the pure compound 10a, 130 mg in 40% yield.
45% With acetic anhydride; triethylamine; at 140℃; for 12h; In a three-necked 100ml flask was added 3,4,5-trimethoxy phenyl acetic acid (2.4g, 10.6mmol), 3- nitro-4-methoxybenzaldehyde (1.92g, 10.6mmol), 2.4ml triethylamine amine and 24ml of acetic anhydride, heated with stirring to 140 , reaction 12h, heating was stopped, 14.4ml of concentrated hydrochloric acid was added dropwise, at room temperature overnight.There khaki solid precipitation, the reaction was stopped, filtered solids with about 150ml recrystallized from ethanol to give yellow needles of pure product 1.86g, yield 45.0%
A mixture of 3,4,5-trimethoxyphenylacetic acid (8.84 mmol) and 3-nitro-4-methoxyenzaldehyde (4.4 mmol), acetic anhydride (4 mL) and triethylamine (2 mL) were heated under reflux for 3 h. After acidification with concentrated hydrochloric acid (6 mL), the resulting solid was filtered off and recrystallised from ethanol to give acrylic acid intermediate 11 as fine yellow needles. Subsequently the corresponding acrylic acid intermediate (5.56 mmol) was added to powdered copper (28.8 mmol) in quinoline (20 mL), and the resulting mixture was heated at 140 C for 2 h. Upon cooling, diethyl ether was added, and the copper was filtered off through Celite. The filtrate was washed with 1 M hydrochloric acid, and the aqueous layer was separated and extracted with diethyl ether. The combined organic layers were washed with saturated aqueous sodium carbonate, water, brine, dried (MgSO4), and concentrated in vacuo. Flash column chromatography (SiO2 petrol/EtOAc 7:3) and recrystallization from EtOAc and petrol afforded desired intermediate compound 12 in 52% yields.
  • 6
  • [ 61240-20-8 ]
  • [ 31680-08-7 ]
  • [ 162705-13-7 ]
YieldReaction ConditionsOperation in experiment
39% NaH (1.54 g, 64.2 mmol) was added into an oven-dried round-bottom reaction flask. AnhydrousCH2Cl2 (100 mL) and 3,4,5-trimethoxybenzyltriphenylphosphonium bromide (6.94 g, 13.3mmol) were added to the reaction flask, and the reaction mixture was stirred for 1 h. The reactionmixture was cooled to -15 C, and <strong>[31680-08-7]4-methoxy-3-nitrobenzaldehyde</strong> (2.01 g 11.1 mmol) wasadded to the reaction flask. The reaction mixture was stirred for 20 h while warming to ambienttemperature under N2. Water (100 mL) was slowly added to the reaction, and the product wasextracted with CH2Cl2 (3 × 100 mL). The organic phase was rinsed with brine, dried withNa2SO4, and concentrated under reduced pressure, and the residue was purified by flash columnchromatography using a pre-packed 100 g silica column [solvent A: EtOAc; solvent B: hexanes;gradient: 10%A / 90%B (1 CV), 10%A / 90%B → 70%A / 30%B (10 CV), 70%A / 30%B (5CV); flow rate: 100 mL/min; monitored at 254 and 280 nm] affording 3' CA4-nitro 46 (1.51 g,S24.34 mmol, 39% yield) as a yellow solid.
1.3 g To a solution of compound 4 (4.5 g, 8.6 mmol) in dry CH2Cl2 (100 mL),NaH (1.7 g, 43.1 mmol) was added at 0 C and the mixture stirred at the sametemperature for 0.5 h, and then the compound 5 (1.6 g, 8.6 mmol) in dry CH2Cl2 (20 mL) wasadded to dropwise in reaction. The mixture reaction stirred at room temperaturefor overnight and monitored by TLC. After completion of reaction, the mixturereaction was quenched with ice water, washed with water (200 mL). The organiclayer was dried over anhydrous Na2SO4 and concentratedunder vacuum. The residue was purified on a silica gel column eluted withpetroleum ether/ethyl acetate (20:1= V:V) to give the desired product 6 (1.3 g, yield 43.7%) asa yellow solid. 1HNMR (300 MHz, CDCl3) δ 7.79 (d, J = 11.6 Hz, 1H), 7.43 (d, J= 8.7 Hz, 1H), 6.94 (d, J = 8.7 Hz, 1H), 6.58 (d, J = 12.1 Hz,1H), 6.47 - 6.42(m, 3H), 3.93 (s, 3H), 3.85 (s, 3H), 3.71 (s, 6H). HR-MS (m/z) (ESI): calcd for C18H19NO6 [M+H]+: 346.1291; found: 346.1275.
1.51 g NaH (1.54 g, 64.2 mmol) was added into an oven-dried round-bottom reaction flask. Anhydrous CH2C12 (100 ml) and 3,4,5-trimethoxybenzyltriphenylphosphonium bromide (6.94 g, 13.3 mmol) were added to the reaction flask, and the reaction mixture was stirred for 1 h. The reaction mixture was cooled to -15 C., and <strong>[31680-08-7]4-methoxy-3-nitrobenzaldehyde</strong> (2.01 g 11.1 mmol) was added to the reaction flask. The reaction mixture was stirred for 20 h while warming to ambient temperature under N2. Water (100 mL) was slowly added to the reaction, and the product was extracted with CH2C12 (3×100 mL). The organic phase was rinsed with brine, dried with Na2SO4, and concentrated under reduced pressure, and the residue was purified by flash column chromatography using a pre-packed 100 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 10% A/90% B (1 CV), 10% A/90% B→70% A/30% B (10 CV), 70% A /30% B (5 CV); flow rate: 100 mL/min; monitored at 254 and 280 nm affording 3′ CA4-nitro (1.51 g,
  • 7
  • [ 24313-88-0 ]
  • [ 31680-08-7 ]
  • [ 709014-07-3 ]
YieldReaction ConditionsOperation in experiment
88% In ethanol; for 3h;Reflux; General procedure: The appropriate amine (10 mmol) was heated at reflux with the appropriate aldehyde (10 mmol) in ethanol (50 mL) for 3 h. The reaction mixture was reduced in vacuo and the resulting solution was left to stand until solid product crystallised. The resulting imine was recrystallised from ethanol.
In ethanol; at 80℃; for 6h; General procedure: A solution of various aromatic aldehydes A1-A10 (1.0 mmol, 1.0 eq) and 3,4,5-trimethoxyaniline (1.0 mmol, 1.0 eq) were added into EtOH (20 ml) at 80 C for 6 h. When the reactions were complete, organic phases were collected to give crude the products C1-C10 without further purified with column chromatography. A solution of compounds C1-C10 (1.0 mmol,1.0 eq), benzoic acid (1.0 mmol, 1.0 eq) and NaBH4 (1.0 mmol, 1.0 eq) were added into DCM (20 ml) at 25 C for 8 h. When the reactions were complete, organic phases were collected to obtain crude products and then were purified by column chromatography to obtain compounds D1-D10. A solution of compounds D1-D10 (1.0 mmol, 1.0 eq) and acyl chloride derivatives (1.0 mmol, 1.0 eq) were added into DMF (8 ml) at 25 C for 6-8 h. Then using EA (20 ml) extracted aqueous layers for three times. Collected organic layers were washed by saturated salt water, dried over magnesium sulfate anhydrous and evaporated to get crude products. Crude products were purified by column chromatography to obtain compounds E1-E11.
  • 8
  • [ 17145-91-4 ]
  • [ 31680-08-7 ]
  • [ 334015-21-3 ]
  • 9
  • [ 24131-30-4 ]
  • [ 31680-08-7 ]
  • (Z)-1-[2-(3,5-dimethoxyphenyl)-ethenyl]-4-methoxy-3-nitrobenzene [ No CAS ]
  • (E)-1-[2-(3,5-dimethoxyphenyl)-ethenyl]-4-methoxy-3-nitrobenzene [ No CAS ]
  • 10
  • [ 61240-20-8 ]
  • [ 31680-08-7 ]
  • [ 162705-13-7 ]
  • [ 206649-07-2 ]
YieldReaction ConditionsOperation in experiment
34%; 50% A mixture of 3,4,5-trimethoxybenzyltriphenylphosphoniumbromide [22] (1.57 g, 3 mmol), powdered potassiumcarbonate (1.38 g, 10 mmol) and 18-crown-6 (0.01 g,0.04 mmol) in dichloromethane (20 mL) was stirred at roomtemperature for 10 min. Then, <strong>[31680-08-7]4-methoxy-3-nitrobenzaldehyde</strong>(0.54 g, 3 mmol) was added and the reaction mixturewas refluxed for 6 h (monitored by TLC). The inorganicsalts were filtered after cooling and the filtrate was concentratedunder reduced pressure to give a mixture of isomers1, 2 and triphenylphosphine oxide. Recrystallization ofthe crude reaction mixture from ethanol afforded pure Estilbene1 (0.40 g, 38 % yield). Column chromatography ofthe mother liquors (petroleum ether/acetone, 15:1 v/v) gaveZ-isomer 2 (0.35 g, 34 % yield) and 1 (0.12 g, 12 % yield). (E)-5-(4-Methoxy-3-nitrostyryl)-1,2,3-trimethoxybenzene(1)Orange crystals. Rf = 0.52. Mp: 151-153 C. 1H NMR(CDCl3, 300 MHz): δ 3.87 (s, 3H, OCH3), 3.91 (s, 6H,OCH3), 3.98 (s, 3H, OCH3), 6.72 (s, 2H, ArH), 6.91 (d, 1H,J = 16.3 Hz, = CH), 6.99 (d, 1H, J = 16.3 Hz, = CH),7.08 (d, 1H, J = 8.7 Hz, ArH), 7.64 (dd, 1H, J = 1.6 Hz,J = 8.7 Hz, ArH), 7.99 (d, 1H, J = 1.6 Hz, ArH). 13CNMR (CDCl3, 75 MHz): δ 55.9; 56.5; 60.8; 103.5; 113.6;122.9; 124.9; 129.3; 130.1; 131.6; 132.1; 138.1; 139.6;151.9; 153.3.(Z)-5-(4-Methoxy-3-nitrostyryl)-1,2,3-trimethoxybenzene(2)Yellow crystals. Rf = 0.58. Mp: 122-123 C. Lit. Mp:123-124 C [12]. 1H NMR (CDCl3, 300 MHz): δ 3.70 (s,6H, OCH3), 3.84 (s, 3H, OCH3), 3.92 (s, 3H, OCH3),6.41-6.46 (m, 3H, ArH, = CH), 6.57 (d, 1H,J = 12.1 Hz, = CH), 6.94 (d, 1H, J = 8.7 Hz, ArH), 7.42(dd, 1H, J = 2.2 Hz, J = 8.7 Hz, ArH), 7.78 (d, 1H,J = 2.2 Hz, ArH). 13C NMR (CDCl3, 75 MHz): δ 55.9;56.5; 60.9; 105.8; 113.1; 125.9; 126.8; 129.7; 131.3; 131.7;134.6; 137.7; 139.4; 151.6; 153.8.
Step (i) :A solution of sodium methoxide (5.66 kg, 29.34 mol) is run into a mixture, at a temperature of 5-10 C., comprising toluene (91.1 litres), trimethoxybenzylphosphonium bromide (15.35 kg, 29.33 mol) and <strong>[31680-08-7]4-methoxy-3-nitrobenzaldehyde</strong> (5.06 kg, 27.93 mol). At the end of the reaction, 0.32 litre (5.59 mol) of acetic acid is run in. After the medium has been maintained at 20 C., it is filtered. The cake is washed with toluene (11.1 litres). The filtrates are washed several times with water (20.2 litres) and then concentrated under vacuum. Isopropyl alcohol (87.6 litres) is then introduced and the medium is concentrated and then cooled. The suspension is then filtered at 10 C. The isolated product is dried under vacuum (6.46 kg, 52.2%). The purity of the isolated product is of the order of 78% with respect to (Z) and 22% with respect to (E).
With sodium hydride; In dichloromethane; at 0 - 20℃; General procedure: To a stirred solution of nitrobenzaldehydes (10, 11, 19, 1 mmol) and 3,4,5-trimethoxybenzyl triphenylphosphonium bromide (9, 1.1 mmol) in anhydrous dichloromethane, sodium hydride (4 mmol) was added at 0 C. The reaction mixture was stirred at room temperature for 18 h and monitored by TLC. After completion of the reaction appropriate amount of water, until foaming stopped, was added at 0 C. The organic layer was separated and the aqueous layer was extracted with chloroform. The combined organic layers were washed with brine solution, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure to get crude compounds, nitro Z-and E-stilbenes isomeric mixture. The isomers were separated by using column chromatographyto give pure Z-stilbenes.
  • 11
  • [13C3]malonic acid [ No CAS ]
  • [ 31680-08-7 ]
  • 3-(4-methoxy-3-nitrophenyl)-E-[1,2-13C2]prop-2-enoic acid [ No CAS ]
  • 12
  • [ 133095-91-7 ]
  • [ 31680-08-7 ]
  • [ 757962-00-8 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; at 0 - 20℃; for 1.16667h; A solution of 3,4,5-trimethoxyphenylmagnesium bromide (11, 1.5eq, 0.5M in THF) was added slowly to the aldehydes 8 and 10 (5 g, 27.6 mmol and 23.6 respectively) in dry THF (10 mL) at 0 C. The reaction mixture was warmed to room temperature, and stirring was continued for another 1 h. A saturated NH4Cl solution was slowly added at 0 C to hydrolyze the adduct and extracted with EtOAc (75 mL x 2). The combined organic extracts were dried over MgSO4 and evaporated to give crude residues 12 & 13.
  • 13
  • [ 75-08-1 ]
  • [ 31680-08-7 ]
  • 4-(bis-ethylsulfanyl-methyl)-1-methoxy-2-nitro-benzene [ No CAS ]
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Technical Information

? Acidity of Phenols ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Chan-Lam Coupling Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? Grignard Reaction ? Halogenation of Phenols ? Hantzsch Dihydropyridine Synthesis ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Julia-Kocienski Olefination ? Knoevenagel Condensation ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mukaiyama Aldol Reaction ? Nomenclature of Ethers ? Nozaki-Hiyama-Kishi Reaction ? Oxidation of Phenols ? Passerini Reaction ? Paternò-Büchi Reaction ? Pechmann Coumarin Synthesis ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Preparation of Ethers ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Ethers ? Reformatsky Reaction ? Reimer-Tiemann Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Stetter Reaction ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction
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; ;