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[ CAS No. 3929-47-3 ] {[proInfo.proName]}

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Chemical Structure| 3929-47-3
Chemical Structure| 3929-47-3
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Product Details of [ 3929-47-3 ]

CAS No. :3929-47-3 MDL No. :MFCD00002951
Formula : C11H16O3 Boiling Point : -
Linear Structure Formula :(CH3O)2C6H3C2H4CH2OH InChI Key :ZISWRXJZUKDIOO-UHFFFAOYSA-N
M.W : 196.24 Pubchem ID :77528
Synonyms :

Safety of [ 3929-47-3 ]

Signal Word:Warning Class:
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 3929-47-3 ]

* 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 [ 3929-47-3 ]

[ 3929-47-3 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 3929-47-3 ]
  • [ 20716-22-7 ]
YieldReaction ConditionsOperation in experiment
95% With nitric acid; In dichloromethane; at 0℃; for 0.5h; Example 3: A general experimental procedure for the preparation of o-nitrohydrocinnamyl alcohol (8b-e) To a stirred solution of alcohol 7b-e (10 mmol) in CH2CI2 (40 mL), cone. HNO3 (2 mL, d =1.4) was added dropwise at 0 C. Reaction mixture was stirred for 30 min and the progress of reaction was monitored by TLC. After completion of reaction, 50 mL of water was added. Organic layer was separated and aqueous layer was extracted with CH2CI2 (2 x 50 mL). Combined organic layers were washed with brine (50 mL), dried over anhydrous Na2S04 and then passed through a thick pad of silica gel (230-400 mesh) with CH^C^ as eluent. The organic layer was concentrated under reduced pressure to give 8b-e in pure form. Example 4: 3-(4,5-Dimethoxy-2-nitrophenyl)propan-1 -ol (8b) Yield: 95% (2.3 g); gum, IR (CHCl3): umax 745, 945, 1 120, 1378, 3412 cm"1; 1H NMR (200 MHz, CDCI3): 1.87-1 .95 (m, 2H), 2.97-3.05 (m, 2H), 3.71 (t, J = 6.2 Hz, 2H), 3.92 (s, 3H), 3.94 (s, 3H), 6.74 (s, 1 H), 7.57 (s, 1 H); 3C NMR (50 MHz, CDCl3): δ 30.1 , 33.5, 56.2, 61 .9, 108.2, 113.4, 132.4, 141.2, 147.2, 153.0; Anal. Calcd for C H15N05 requires C, 54.77; H, 6.27; N, 5.81 ; found C, 54.86; H, 6.33; N, 5.87%.
95% With nitric acid; In dichloromethane; at 0℃; for 0.5h; General procedure: To a stirred solution of alcohol 7b-e (10 mmol) in CH2Cl2 (40 mL), conc. HNO3 (2 mL, d=1.4) was added dropwise at 0 C. Reaction mixture was stirred for 30 min and the progress of reaction was monitored by TLC. After completion of reaction, 50 mL of water was added. Organic layer was separated and aqueous layer was extracted with CH2Cl2 (2×50 mL). Combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4 and then passed through a thick pad of silica gel (230-400 mesh) with CH2Cl2 as eluent. The organic layer was concentrated under reduced pressure to give 8b-e in pure form.
  • 2
  • [ 5462-13-5 ]
  • [ 3929-47-3 ]
  • 3
  • [ 3929-47-3 ]
  • [ 3945-85-5 ]
YieldReaction ConditionsOperation in experiment
99% With N-Bromosuccinimide; triphenylphosphine; In dichloromethane; at 0℃; for 1h; Triphenylphosphine (802 mg, 3.06mmol) and N-bromosuccinimide (544 mg, 3.06 mmol) were added to a solution of 3-(3,4-Dimethoxyphenyl)-1-propanol (500 mg, 2.55 mmol) in CH2Cl2 (10 mL) at 0 C under nitrogenatmosphere. The reaction mixture was stirred at 0 C for 1 h. The reaction was quenched with saturated aqueous solution of NaHCO3 (10 mL) and extracted from theaqueous phase with MC (10 mL x 3). The organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by flash column chromatography(40% EtOAc/hexane) to yield 655 mg (2.53 mmol, 99%) of 4-(3-bromopropyl)-1,2-dimethoxybenzene as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 2.06-2.13 (m, 2H),2.68 (t, J = 7.3 Hz, 2H), 3.34 (t, J = 6.5 Hz, 2H), 3.81 (s, 3H), 3.83 (s, 3H), 6.69-6.71 (m, 2H),6.76 (d, J = 8.5 Hz, 1H); 13C NMR(100 MHz, CDCl3) δ 33.03, 33.36, 34.17, 55.69, 55.76, 111.23,111.74, 120.27, 132.93, 147.29, 148.78; MS (EI) 258 (M+), 260 (M+), 151 (100); HRMS (EI) calcdfor C11H1579BrO2 (M+) 258.0255, found 258.0254.
87% With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0℃; for 2h; After 3 (7.60 g, 38.73 mmol) was dissolved in dichloromethane (DCM) (50 mL), along with CBr4 (13.50 g, 40.67 mmol), the reaction mixture was cooled to 0C, and PPh3 (10.68 g, 40.67 mmol) was added slowly. The resultant reaction solution was stirred for 2 h,and the reaction solvents were removed under reduced pressure. The residue was purified by flash column chromatography (petroleumether/EtOAc) to produce a colorless oil (4, 8.72 g, 87%).
84% With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0℃; for 4h; To a solution of <strong>[3929-47-3]3-(3,4-dimethoxyphenyl)propan-1-ol</strong> (3.6 g, 18.36 mmol) and CBr4 (6.09 g, 18.36 mmol) in DCM (20 mL) was added PPh3 (4.7 g, 18 mmol) and the reaction was stirred at 0 oC for 4 hrs. The reaction mixture was poured into H2O (100 mL) and extracted with DCM (50 mL x 3). The combined DCM layers were washed with brine (150 mL), dried over Na2SO4 and concentrated to dryness in vacuum. The residue was purified by silica gel column (PE/EA = 7/1) to give 4-(3-bromopropyl)-1,2-dimethoxybenzene (4 g, yield: 84%) as a colorless oil.
EXAMPLE 24A 1-Bromo-3-(3,4-dimethoxyphenyl)propane The title compound was prepared from <strong>[3929-47-3]3-(3,4-dimethoxyphenyl)-1-propanol</strong> as described in Journal of the American Chemical Society, 95, 8749 (1973), which is incorporated herein by reference, to provide the title compound. MS (DCI/NH3) m/e 276 (M+NH4)+.
With N-Bromosuccinimide; triphenylphosphine; In dichloromethane; at 20℃; for 16h;Ice-cooling; (18-2) Synthesis of 1-(3-bromopropyl)-3,4-dimethoxybenzene (compound 18-2) Compound 18-1 (2.00 g) was dissolved in methylene chloride (50 ml), triphenylphosphine (2.97 g) and N-bromosuccinimide (1.99 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 1 hr, and further at room temperature for 15 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether (100 ml) was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=5:1 - 3:1) to give the object product (2.17 g) as a pale-brown oil. 1H-NMR(CDCl3) δ (ppm): 2.11-2.18(2H, m), 2.73(2H, t, J=7.3Hz), 3.40(2H, t, J=6.5Hz), 3.86(3H, s), 3.88(3H, s), 6.72-6.75(2H, m), 6.79-6.81(1H, m).

  • 4
  • [ 2107-70-2 ]
  • [ 3929-47-3 ]
YieldReaction ConditionsOperation in experiment
100% With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 75℃; for 1.5h; To a solution of 3-(3,4-dimethoxyphenyl)-propionic acid (0.50 g, 2.38 mmol) in 10 mL THF, (CH3)2SBH3 (0.3 mL, 3.57 mmol) was added at 0 C and the mixture was stirred at 75 C for 1.5 h. After the completion of the reaction, excess of (CH3)2SBH3 was quenched by addition of CH3OH at 0 C and then the solvent was evaporated in vacuo. The product was used in the following step without further purification (0.47 g, 100%). 'H NMR (300 MHz, CDCb) d: 6.80 - 6.71 (m, 3H, AT-H), 3.85 (s, 3H, -OC//3), 3.84 (s, 3H, -OC//3), 3.66 (t, = 6.4 Hz, 2H, -C//2OH), 2.64 - 2.62 (m, 2H, -C//2CH2CH2OH), 1.91 - 1.81 (m, 2H, -CH2C//2CH20H).13C NMR (75 MHz, CDCI3) d: 148.9, 147.2, 134.5, 120.2, 11 1.8, 1 1 1.3, 62.3, 56.0, 55.9, 34.5, 31.8. MS m/z: 196.91 (M+H)+, 218.99 (M+Na)+, 414.67 (2M+Na)+
92% With dimethylsulfide borane complex; In tetrahydrofuran; at 0℃; for 4h;Inert atmosphere; To a solution of 3-(3,4-dimethoxyphenyl)propanoic acid (4.2 g, 20 mmol) in THF (20 mL) was added BH3-DMS (10M, 2.2 mL, 22 mmol) and the reaction was stirred at 0 oC under N2 for 4 hrs. The reaction mixture was quenched with MeOH (5 mL) and concentrated to dryness in vacuum. After that, the dry mixture was poured into H2O (100 mL) and extracted with DCM (50 mL x 3). The combined DCM layers were washed with brine (100 mL), dried over Na2SO4 and concentrated to give 3-(3,4-dimethoxyphenyl)propan-1-ol (3.6 g, yield: 92%) as a colorless oil.
88.6% With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 0 - 60℃; for 10h; Compound 3a (11.0 g, 52.3 mmol) was dissolved in 80 ml of tetrahydrofuran and precooled in a 0 C low temperature bath. willSodium borohydride (5.9 g, 157.0 mmol) was added portionwise to the above reaction mixture, and then iodine (13.3 g, 52.3 mmol) in tetrahydrofuran (40 ml) was slowly added dropwise to the reaction mixture. The iodine was consumed completely and there was no gas overflow, and the reaction solution was transferred to a 60 C oil bath for heating for 10 hours. The reaction was monitored by TLC until compound 3a was completely reacted. 30 ml of methanol was slowly added to the reaction solution at 0 C to quench the reaction. After the reaction mixture was poured into 200 ml of water and extracted with dichloromethane (80 ml) three times, the organic phase was combined, and the organic phase was back-washed with saturated brine. The organic phase was dried over anhydrous sodium sulfate and dried.The crude product was purified by flash silica gel column (PE/EA=12/1) The yield was 88.6%.
A solution of 6.0 g (28.5 mmol) 3- (3, 4-dimethoxyphenyl) -propionic acid in 120 ml anhydrous THF is cooled to 0 C and treated within 15 minutes with 42.75 ml borane THF complex (1 M solution). Stirring is continued overnight at rt. The resulting clear solution is cooled with an ice/water bath and hydrolyzed by the addition of 100 ml saturated ammonium chloride solution. Extractive work-up with diethyl ether furnishes a colourless oil, which is purified by chromatography (HEXANE/ETHYL acetate) to yield a colourless oil. 1H-NMR (300 MHz, CDC13) : 6.76-6. 80 (m, 1H), 6.70-6. 74 (m, 2H), 3.86 (s, 3H), 3.85 (s, 3H), 3.67 (t, 2H), 2.62-2. 69 (m, 2H), 1.82-1. 93 (m, 2H). MS: 197 (M+1) +
With dimethylsulfide borane complex; In tetrahydrofuran; diethyl ether; at 20℃; Step 2. 3-(3,4-dimethoxyphenyl)propanoic acid was dissolved in THF (100 mL). Borane-dimethyl sulfide complex (2M in diethyl ether, 20 mL, 40 mmol) was added. The reaction mixture was stirred overnight at room temperature. Methanol was added slowly to quench the reaction mixture, then silica was added and the volatiles were removed under reduced pressure. The residue was purified on silica using a heptane to ethyl acetate gradient yielding the product as an oil. This was used as such in the next step.LC-MS: Anal. Calcd. For CnHie03: 196.1 1 ; found 195[M-H]
With dimethylsulfide borane complex; In tetrahydrofuran; diethyl ether; at 20℃; 10129] Step 2. 3-(3,4-dimethoxyphenyl)propanoic acid was dissolved in THF (100 mE). l3orane-dimethyl sulfide complex (2M in diethyl ether, 20 mE, 40 mmol) was added. The reaction mixture was stirred overnight at room temperature. Methanol was added slowly to quench the reaction mixture, then silica was added and the volatiles were removed under reduced pressure. The residue was purified on silica using a heptane to ethyl acetate gradient yielding the product as an oil. This was used as such in the next step.10130] EC-MS: Anal. Calcd. For C, ,H,503: 196.11; found195[M-H]

  • 7
  • [ 27798-73-8 ]
  • [ 3929-47-3 ]
YieldReaction ConditionsOperation in experiment
74.8% With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 2.5h; General procedure: A mixture of Lithium aluminum hydride (9.5 g, 0.250 mol), dry THF(250 mL), to it add substituted dihydrocinnamic acid methyl ester (3ae,0.127 mol), in THF (50 mL) was added slowly drop wise during30 min. After completion of addition the reaction mixture was stirredfor 2 h at rt, after completion of reaction as monitored by TLC hexane/ethyl acetate (8:2), the reaction mixture was poured in water (200 mL),acidified with 5 N HCl, extract with chloroform (2×400 mL), extractwas wash with water, brine solution, dried over Na2SO4 and concentrated.The crude residue was subjected to column chromatographyon silica gel, column was eluted with hexane/ethyl acetate mixtures,pure compound was eluted in ethyl acetate in hexane, 10%/90% (v/v)which was monitored by TLC, pure fractions were combined and concentratedto obtained 3-(substituted phenyl)- propan-1-ol as oily compoundswith yields of 73-77%.
  • 8
  • [ 61871-67-8 ]
  • [ 3929-47-3 ]
  • 9
  • [ 3929-47-3 ]
  • [ 2032-35-1 ]
  • [ 70821-95-3 ]
  • 10
  • [ 3929-47-3 ]
  • [ 2032-35-1 ]
  • [ 70821-95-3 ]
  • [ 79242-33-4 ]
  • 11
  • [ 38078-09-0 ]
  • [ 3929-47-3 ]
  • 1,2-Dimethoxyphenyl-4-(3-fluoropropyl)benzene [ No CAS ]
  • 3,4-Dimethoxybenzenepropanol diethylamidosulfite [ No CAS ]
  • Bis<3-(3,4-dimethoxyphenyl)propyl> carbonate [ No CAS ]
  • 12
  • [ 3929-47-3 ]
  • [ 144-55-8 ]
  • 1,2-Dimethoxyphenyl-4-(3-fluoropropyl)benzene [ No CAS ]
  • 3,4-Dimethoxybenzenepropanol diethylamidosulfite [ No CAS ]
  • Bis<3-(3,4-dimethoxyphenyl)propyl> carbonate [ No CAS ]
  • 13
  • [ 3929-47-3 ]
  • [ 61871-67-8 ]
YieldReaction ConditionsOperation in experiment
92% With dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; at 20℃; for 3h; Toa stirred solution of IBX (7.1g, 25.51 mmol) in dry DMSO (5 mL) was added a solution of 2 (2.5 g, 12.75 mmol) in dry DCM (20 mL) at room temperature andstirred for 3h at room temperature.After completion of the reaction, the mixture was filtered and dilutedwith ice cold water (10 mL) and extracted into DCM (2 x 30 mL). The combinedorganic layer was washed with brine (20 mL), dried over anhydrous Na2SO4and evaporated to give crude aldehyde (2.27 g, Yield 92%), which wasused directly for next step without purification.
77.4% With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; General procedure: Suitable 3-(substituted-phenyl)-propan-1-ol (4a-e, 0.02727 mol)compound was dissolved in DMSO (150 mL) and to the mixture IBX(28 g, 0.02727 mol) was added portion wise during 45 min. Aftercompletion of addition, the reaction mixture was stirred for 2 h. at roomtemperature. After completion of reaction which was monitored by TLChexane/ethyl acetate (8:2), the reaction mixture was poured into water(200 mL). The mixture was filter off; the filter bed was washed withchloroform (200 mL). The filtrate was taken in to a separating funnel,separated the organic layer and the aqueous layer was extracted withchloroform (200 mL). The combined organic layer was washed withwater, brine solution, dried over Na2SO4 and concentrated under vacuum.The crude residue was subjected to column chromatography onsilica gel, using ethyl acetate in hexane, 15%/85% (v/v) eluents asmonitored by TLC, pure fractions were combined and concentrated toobtained 3-(substituted-phenyl)-propan-1-al as oily compounds withyields of (5a-e, 73-81%).
60% With pyridinium chlorochromate; In dichloromethane; at 0 - 20℃; for 2h; To a solution of PCC (0.43 g, 2.0 mmol) in dry CH2Cl2 (4 mL), a solution of <strong>[3929-47-3]3-(3,4-dimethoxyphenyl)propan-1-ol</strong> (0.30 g, 1.54 mmol) in dry CH2C12 (6 mL), was added at 0 C. The mixture was stirred at ambient temperature for 2 h. After the completion of the reaction, themixture was filtered through a pad of celite using Et20. The filtrate was concentrated in vacuo and the desired product was afforded as colorless oil and used without further purification, (0.18 g, 60%). ‘H NMR(600 MHz, CDCl3) (5: 9.76 (s, 1H, -CHO), 6.75 - 6.68 (m, 3H, Ar-fl), 3.82 (s, 3H, -OCH3), 3.80 (s, 3H,OCH3), 2.86 (t, J 7.5 Hz, 2H, -CH2CH2CHO), 2.73 - 2.70 (m, 2H, -CH2CH2CHO).’3C NMR (75 MHz, CDCI3) (5: 201.6, 148.9, 147.5, 132.9, 120.1, 111.7, 111.4, 55.9, 55.8, 45.4, 27.7. MS m/z: 411.12(2M+Na)
With Dess-Martin periodane; In dichloromethane; for 0.5h; A solution of 2.0 g (10. 2 MMOL) OF THE aldehyde prepared in step A in 40 ml CH2C12 is oxidised in the dark by the addition of 4.32 g (10.2 mmol) Dess-Marin periodinane. The reaction is complete after 30 minutes. The suspension formed is taken up into 50 ml CH2CL2 and washed twice with sodium bicarbonate and 20 % sodium thiosulphate solution. Concentration of the organic layer affords a beige crude product which is purified by chromatography (hexane/ethyl acetate) to yield a yellow oil. IH-NMR (300 MHz, CDC13) : 9. 80 (t, 1H), 6.70-6. 81 (m, 5H), 3.86 (s, 3H), 3.85 (s, 3H), 3.87-3. 94 (m, 2H), 2.72-2. 80 (m, 2H). MS: 193 (M+1) +

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