| 99% |
With dichlorosulfoxide at 0 - 75℃; for 2h; |
18.B b) Step-B: Preparation of ethyl (E)-3-(4-fluorophenyl)acrylate:
To a stirred solution of (E)-3-(4-fluorophenyl)acrylic acid (5 g, 30.1 mmol) in ethanol (50 mL), thionyl chloride (3.3 mL, 45.1 mmol) was added at 0 °C. The resulting reaction mixture was allowed to stir at 75 °C for 2 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure. The residue obtained was diluted with water (40 mL) and basified with saturated solution of sodium bicarbonate (30 mL). The reaction mass extracted with dichloromethane (2 x 50 mL). The combined organic layers were washed with brine solution (30 mL), dried over anhydrous sodium sulphate and evaporated under reduced pressure to obtain a crude compound, which was purified by column chromatography to obtain ethyl (E)-3-(4-fluorophenyl)acrylate (5.8 g, 29.9 mmol, 99 % yield). 1H-NMR (400 MHz, DMSO-D6): δ 7.79 (ddd, J = 11.9, 5.3, 3.2 Hz, 2H), 7.64 (d, J = 15.9 Hz, 1H), 7.28-7.22 (m, 2H), 6.62-6.58 (m, 1H), 4.18 (q, J = 7.1Hz, 2H), 1.24 (td, J = 7.2, 4.9 Hz, 3H). |
| 99% |
With dichlorosulfoxide at 0 - 75℃; for 2h; |
18.B b) Step-B: Preparation of ethyl (E)-3-(4-fluorophenyl)acrylate:
To a stirred solution of (E)-3-(4-fluorophenyl)acrylic acid (5 g, 30.1 mmol) in ethanol (50 mL), thionyl chloride (3.3 mL, 45.1 mmol) was added at 0 °C. The resulting reaction mixture was allowed to stir at 75 °C for 2 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure. The residue obtained was diluted with water (40 mL) and basified with saturated solution of sodium bicarbonate (30 mL). The reaction mass extracted with dichloromethane (2 x 50 mL). The combined organic layers were washed with brine solution (30 mL), dried over anhydrous sodium sulphate and evaporated under reduced pressure to obtain a crude compound, which was purified by column chromatography to obtain ethyl (E)-3-(4-fluorophenyl)acrylate (5.8 g, 29.9 mmol, 99 % yield). 1H-NMR (400 MHz, DMSO-D6): δ 7.79 (ddd, J = 11.9, 5.3, 3.2 Hz, 2H), 7.64 (d, J = 15.9 Hz, 1H), 7.28-7.22 (m, 2H), 6.62-6.58 (m, 1H), 4.18 (q, J = 7.1Hz, 2H), 1.24 (td, J = 7.2, 4.9 Hz, 3H). |
| 66% |
With sulfuric acid for 30h; Reflux; |
2.1. Synthesis and Characterization
General procedure: A series of 4- or 3-substituted ethyl-cinnamates was prepared by conventional method [38], using 2 mmol of para and meta substituted cinnamic acids refluxed in absolute ethanol (15 mL) and sulfuric acid (0.1 mL) for 30 h. The ester formation was monitored by GC and TLC (hexane:acetate 9:1 as eluent). The products were isolated after washing with aqueous sodium bicarbonate solution and solvent extraction with dichloromethane. After work up and solvent evaporation, most of the pure esters were obtained as an oil or a solid. All compounds were characterized by 1H and 13C-NMR spectroscopy, in agreement with the literature [39-41]. The spectroscopic and characterization information of all compounds is given as Electronic Supplementary Information. |
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