ethyl 2-[4-(chloromethyl)phenyl]propanoate

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: After a solution of 15 g of sodium iodide in 140 ml of methyl ethyl ketone was refluxed for 1 hour, 12.5 g of ethyl 2-(4-chloromethylphenyl)propionate was added and refluxing was continued for further 8 hours. After the reaction was completed, methyl ethyl ketone was removed by distillation from the reaction mixture under reduced pressure, the residue was poured into ice-water and extracted with ether. The extract was washed with water and an aqueous sodium thiosulfate solution, successively, dried, and the solvent was evaporated to give 16.3 g of the desired compound as an oily and slightly yellow substance. refluxing methyl ethyl ketone was removed by distillation from the reaction mixture under reduced pressure the residue was poured into ice-water extracted with ether The extract was washed with water an aqueous sodium thiosulfate solution, successively, dried the solvent was evaporated

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 9.6 g of 50% sodium hydride and 200 ml of dimethyl formamide was added dropwise 34 g of ethyl 2-cyclohexanone carboxylate under ice-cooling, the mixture was stirred at 50° C. for 30 minutes, thereafter again under ice-cooling 45.3 g of ethyl 2-(p-chloromethylphenyl)propionate was added dropwise, and the mixture was heated at 50°-60° C. with stirring for 1 hour. After the reaction was completed, the reaction mixture was poured into an ice-water, extracted with ether, the extract washed with water, dried over anhydrous sodium sulfate, and the solvent removed by distillation to give 69.5 g of an oily substance, which was subjected to a vacuum distillation affording 57 g of the dsired compound as a colorless oily substance, b.p. 200°-205° C. at 0.4 mm Hg. cooling was added dropwise the mixture was heated at 50°-60° C. with stirring for 1 hour extracted with ether the extract washed with water dried over anhydrous sodium sulfate the solvent removed by distillation to give 69.5 g of an oily substance, which was subjected to a vacuum distillation

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 9.6 g of 50% sodium hydride and 200 ml of dimethyl formamide was added dropwise 34 g of ethyl 2-cyclohexanone carboxylate under ice-cooling, the mixture was stirred at 50° C. for 30 minutes, thereafter again under ice-cooling 45.3 g of ethyl 2-(p-chloromethylphenyl)propionate was added dropwise, and the mixture was heated at 50°-60° C. with stirring for 1 hour. After the reaction was completed, the reaction mixture was poured into an ice-water, extracted with ether, the extract washed with water, dried over anhydrous sodium sulfate, and the solvent removed by distillation to give 69.5 g of an oily substance, which was subjected to a vacuum distillation affording 57 g of the dsired compound as a colorless oily substance, b.p. 200°-205° C. at 0.4 mm Hg. cooling was added dropwise the mixture was heated at 50°-60° C. with stirring for 1 hour extracted with ether the extract washed with water dried over anhydrous sodium sulfate the solvent removed by distillation to give 69.5 g of an oily substance, which was subjected to a vacuum distillation

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

Procedure: To 200 ml of dimethyl formamide containing 6.0 g of potassium hydroxide was added 15.6 g of 2-carboethoxycyclopentanone with stirring at room temperature to give a homogeneous solution. Under ice-cooling, 25 g of ethyl 2-(p-chloromethylphenyl)propionate was added dropwise thereto, and the mixture was heated at 80° C. with stirring for 2 hours. After completion of the reaction, the reaction mixture was poured into an ice-water, extracted with ether, the extract washed with water, dried over anhydrous sodium sulfate, and the solvent removed by distillation to give 28 g of an oily substance, which was subjected to a vacuum distillation affording 21 g of the desired compound, b.p. 175°-178° C. at 0.5 mm Hg. to give a homogeneous solution Under ice-cooling the mixture was heated at 80° C. with stirring for 2 hours After completion of the reaction extracted with ether the extract washed with water dried over anhydrous sodium sulfate the solvent removed by distillation to give 28 g of an oily substance, which was subjected to a vacuum distillation

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: After a solution of 15 g of sodium iodide in 140 ml of methyl ethyl ketone was refluxed for 1 hour, 12.5 g of ethyl 2-(4-chloromethylphenyl)propionate was added and refluxing was continued for further 8 hours. After the reaction was completed, methyl ethyl ketone was removed by distillation from the reaction mixture under reduced pressure, the residue was poured into ice-water and extracted with ether. The extract was washed with water and an aqueous sodium thiosulfate solution, successively, dried, and the solvent was evaporated to give 16.3 g of the desired compound as an oily and slightly yellow substance. refluxing methyl ethyl ketone was removed by distillation from the reaction mixture under reduced pressure the residue was poured into ice-water extracted with ether The extract was washed with water an aqueous sodium thiosulfate solution, successively, dried the solvent was evaporated

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 9.6 g of 50% sodium hydride and 200 ml of dimethyl formamide was added dropwise 34 g of ethyl 2-cyclohexanone carboxylate under ice-cooling, the mixture was stirred at 50° C. for 30 minutes, thereafter again under ice-cooling 45.3 g of ethyl 2-(p-chloromethylphenyl)propionate was added dropwise, and the mixture was heated at 50°-60° C. with stirring for 1 hour. After the reaction was completed, the reaction mixture was poured into an ice-water, extracted with ether, the extract washed with water, dried over anhydrous sodium sulfate, and the solvent removed by distillation to give 69.5 g of an oily substance, which was subjected to a vacuum distillation affording 57 g of the dsired compound as a colorless oily substance, b.p. 200°-205° C. at 0.4 mm Hg. cooling was added dropwise the mixture was heated at 50°-60° C. with stirring for 1 hour extracted with ether the extract washed with water dried over anhydrous sodium sulfate the solvent removed by distillation to give 69.5 g of an oily substance, which was subjected to a vacuum distillation

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

Procedure: To 200 ml of dimethyl formamide containing 6.0 g of potassium hydroxide was added 15.6 g of 2-carboethoxycyclopentanone with stirring at room temperature to give a homogeneous solution. Under ice-cooling, 25 g of ethyl 2-(p-chloromethylphenyl)propionate was added dropwise thereto, and the mixture was heated at 80° C. with stirring for 2 hours. After completion of the reaction, the reaction mixture was poured into an ice-water, extracted with ether, the extract washed with water, dried over anhydrous sodium sulfate, and the solvent removed by distillation to give 28 g of an oily substance, which was subjected to a vacuum distillation affording 21 g of the desired compound, b.p. 175°-178° C. at 0.5 mm Hg. to give a homogeneous solution Under ice-cooling the mixture was heated at 80° C. with stirring for 2 hours After completion of the reaction extracted with ether the extract washed with water dried over anhydrous sodium sulfate the solvent removed by distillation to give 28 g of an oily substance, which was subjected to a vacuum distillation