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CAS No. : | 28170-07-2 | MDL No. : | MFCD07784341 |
Formula : | C14H12O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SNGLYCMNDNOLOF-UHFFFAOYSA-N |
M.W : | 228.24 | Pubchem ID : | 11183772 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With pyridine; In dichloromethane; for 4h; | This compound is a known compound, but it is not commercially available. It was prepared by following a published procedure. (Rich et al., J. Org. Chem., 1978, 43, 3624). To a mixture of benzyl alcohol (freshly distilled, 69.2 g, 0.64 mol), pyridine (64 mL) and CH2Cl2 (115 mL) in a 500 mL 3 -necked flask equipped with a condenser, mechanical stirring and an addition funnel was added phenyl chloroformate (100 g, 0.64 mol) over a period of 1 h. The reaction mixture was stirred for an additional 3 h, and H2O (160 mL) was added. The organic phase was washed with aqueous H2SO4 (2 M; 150 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was distilled in vacuum 127-131 C/0.1 mm Hg to give the desired compound as colorless oil, Yield: 108 g (94%) (literature yield: 79%).[0215] 1H NMR (500 MHz, CDCl3, 25 0C): delta 5.37 (s, 2H, CH2), 7.18-7.48 (m, 10 H, ArH). MS (FAB): m/z = 372.1 (MH+). |
91% | With pyridine; In dichloromethane; for 1h; | According to: Pittelkow, M.; Lewinsky, R.; and Christensen, J. B. Synthesis 2002, 15, 2195- 2202.Phenyl chloroformate (54.1 g, 500 mmol) was added dropwise to a mixture of benzyl alcohol (78.3 g, 500 mmol), dichloromethane (90 ml) and pyridine (50 ml) in a 1 l-f lask with condenser and addition funnel. The mixture was stirred for 1 h. Water (125 ml) was added. The phases were separated. The organic phase was washed with dilute sulfuric acid (2 M, 2x125 ml). Brine had to be added in the final wash in order to obtain good separation. The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude compound was vacuum destilled to yield a colourless liquid. Yield:104.3 g, 91 % EPO <DP n="71"/>1H-NMR (CDCI3) delta: 7.46-7.17 (2 multiplthetats, 10H), 5.27 (s, 2H)13C- NMR (CDCI3) delta: 152.5, 149.9, 133.5, 128.3, 127.6, 127.5, 127.3, 124.8, 119.8, 69.1 |
91% | In pyridine; dichloromethane; for 1h; | Benzyl phenyl carbonateAccording to: Pittelkow, M.; Lewinsky, R.; and Christensen, J. B. Synthesis 2002, 15, 2195- 2202.Phenyl chloroformate (54.1 g, 500 mmol) was added dropwise to a mixture of benzyl alcohol (78.3 g, 500 mmol), dichloromethane (90 ml) and pyridine (50 ml) in a 1 l-f lask with condenser and addition funnel. The mixture was stirred for 1 h. Water (125 ml) was added. EPO <DP n="95"/>The phases were separated. The organic phase was washed with dilute sulfuric acid (2 M, 2x125 ml). Brine had to be added in the final wash in order to obtain good separation. The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude compound was vacuum destilled to yield a colourless liquid. Yield:104.3 g, 91 %1H-NMR (CDCI3) delta: 7.46-7.17 (2 multiplets, 10H), 5.27 (s, 2H)13C- NMR (CDCI3) delta: 152.5, 149.9, 133.5, 128.3, 127.6, 127.5, 127.3, 124.8, 119.8, 69.1 |
82% | With triethylamine; In dichloromethane; at 0 - 20℃; for 18h; | In a single-necked flask, benzyl alcohol 38 and triethylamine (1.1 eq) were added and dissolved in dichloromethane with stirring.Phenyl chloroformate 39 (1.0 eq) was weighed and slowly dropped at 0 C. After the addition was complete, stir at room temperature for 18h. The reaction solution was washed with water and dilute hydrochloric acid, and the pH was adjusted to 8 with NaHCO3. The organic phase was dried by adding anhydrous sodium sulfate.Filter and concentrate the filtrate to dryness to obtain the crude product. The crude product was passed through a silica gel column to obtain a transparent oily substance 40 with a yield of about 82% |
62% | With triethylamine; In dichloromethane; at 0 - 20℃; | General procedure: The alcohol, thiol, or amine starting material (1.0 equiv.) was combined with the phenyl chloroformate reagent (1.0 equiv.) in anhydrous CH2Cl2 (15mL) at 0C, followed by the addition of base (1.0 equiv.). The resultant solution was stirred at 0C for 20 min, after which the ice bath was removed, and the reaction mixture was stirred at r.t. until the completion of the reaction as indicated by TLC. The reaction was quenched by adding brine (30mL), and the aqueous solution was extracted with ethyl acetate (3×15 mL). The organic layers were combined, dried over MgSO4, and evaporated under vacuum. The crude products from each reaction were purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | In ethanol; at 20℃; for 2h;Reflux; | A mixture of 1,6-diaminohexane 39 (39.15 g, 0.338 mol) and <strong>[28170-07-2]benzyl phenyl carbonate</strong> (35.7 g, 0.156 mol) inethanol (125 ml) was stirred for 2 hours at room temperature and subsequently heated for an additional hour atreflux to achieve full conversion. The reaction mixture was allowed to cool to room temperature, affording awhite precipitate. After removing the precipitate by filtration, the supernatant was evaporated to dryness anddissolved in 330 ml 2 M aqueous HCl. The resulting solution was extracted with dichloromethane (DCM)(2x150 ml). The aqueous phase was subsequently adjusted to pH = 10 with 6 M aqueous NaOH and extractedwith DCM (3x150 ml). All organic phases were combined, dried over Na2SO4, evaporated to dryness, anddissolved in 200 ml diethyl ether. The resulting solution was extracted with 1M aqueous NaOH (3x50 ml), driedover Na2SO4, and evaporated to dryness to afford crude 40. The product was recrystallized from diethyl ether at-18C to afford white crystals (12.0 g, 31 %). 1H NMR (400 MHz, CDCl3): delta 1.03 (br.s, 2H), 1.58-1.14 (m, 8H),2.66 (t, J = 6.9 Hz, 2H), 3.18 (q, J = 6.7 Hz, 2H), 4.83 (br.s, 1H), 5.08 (s, 2H), 7.45 - 7.19 (m, 5H) ppm. 13CNMR (400 MHz, CDCl3): delta 26.63, 26.68, 30.07, 33.83, 41.12, 42.25, 66.67, 128.17, 128.21, 128.61, 136.78,156.51 ppm. RP-LCMS: calc. Mw= 250.2 g/mol, found m/z: 251.3 [M+H]+.Synthesis of |