(E)-METHYL 3-(2-CHLOROPHENYL)ACRYLATE

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1000 ml round-bottomed flask, equipped with a magnetic stirrer, was filled with 362 ml of tert-butyl alcohol, 362 ml of water, K3Fe(CN)6 (135.53 g, 411.63 mmol), K2CO3 (56.89 g, 411.63 mmol), (DHQ)2PHAL (1.06 g, 1.37 mmol), K2OsO2(OH)4, (0.1 g, 0.27 mmol), and Methanesulfonamide (13.05 g, 137.21 mmol) and stirred at 0° C. (E)-Methyl-3-(2-chlorophenyl)acrylate (26.98 g, Preparation example 24) was added at once, and the mixture was stirred vigorously at 0° C. overnight. While the mixture was stirred at 0° C., solid sodium sulfite (Na2SO3, 24.4 g, 193.5 mmol), EtOAc and water was added and the mixture was allowed to warm to room temperature and stirred. After the separation of the layer, the aqueous layer was added to EtoAc, and the aqueous layer was separated. The combined organic layers were washed with 0.3M H2SO4/Na2SO4 solution (H2SO4 76 ml, H2O 2 L, Na2SO4 360 g) twice. After separation of the organic layer, the organic layer was washed with H2O. After separating of the layer, the organic layer were dried over anhydrous MgSO4, filtered and concentrated under vacuum. The crude compound was purified by a silica gel column to produce the title compound (24.42 g, 7090%) A 1000 ml round-bottomed flask, equipped with a magnetic stirrer was added at once, and the mixture While the mixture was stirred at 0° C. to warm to room temperature stirred After the separation of the layer the aqueous layer was added to EtoAc the aqueous layer was separated The combined organic layers were washed with 0.3M H2SO4/Na2SO4 solution (H2SO4 76 ml, H2O 2 L, Na2SO4 360 g) twice After separation of the organic layer the organic layer was washed with H2O After separating of the layer the organic layer were dried over anhydrous MgSO4 filtered concentrated under vacuum The crude compound was purified by a silica gel column

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 250 ml round-bottomed flask, 2-Chlorocinnamic acid (25 g, 136.9 mmol) and MeOH(56 ml) were added. POCl3 (1.27 ml, 13.6 mmol) was added dropwise. The reaction mixture was stirred under reflux for 3˜4 h. The reaction mixture was cooled to room temperature, quenched with 1N NaOH solution. The mixture was extracted by EtOAc and washed with H2O. The aqueous layer was further extracted with EtOAc. The combined organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under vacuum. (26.98 g, 85˜97%) under reflux for 3˜4 h quenched with 1N NaOH solution The mixture was extracted by EtOAc washed with H2O The aqueous layer was further extracted with EtOAc The combined organic layer was dried over anhydrous magnesium sulfate (MgSO4) filtered concentrated under vacuum