Ethylene Glycol → Benzoic acid, 4-((1,1-dimethyl-2-((3-phenoxyphenyl)methoxy)ethyl))-, ethyl ester

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Reaction Conditions

Reaction Steps

3-Phenoxybenzyl 2-(4-carboethoxyphenyl)-2-methylpropyl ether was synthesized according to the following procedures. (1) A mixture of 3.5 g of 3-phenoxybenzyl 2-(4-cyanophenyl)-2-methylpropyl ether, 7.0 g of potassium hydroxide, 7.0 g of water and 20 ml of ethylene glycol was stirred at 130° C. for 4.0 hours. The mixture was cooled to room temperature, and water was added and the mixture was made acidic by addition of hydrochloric acid. Then, the mixture was extracted with ether, and the ether extract was washed with water, dried over Na2SO4, and evaporated to give 3.1 g of 3-phenoxybenzyl 2-(carboxyphenyl)-2-methylpropyl ether (mp. 98.5°-102.5° C.). (2) A mixture of 1.0 g of 3-phenoxybenzyl 2-(4-carboxyphenyl)-2-methylpropyl ether, 0.6 g of phosphorus pentachloride and 15 ml of benzene was treated at 70° to 80° C. for 30 minutes, and the solvent was removed by distillation under reduced pressure. The obtained crude acid chloride was dissolved in 10 ml of benzene and the solution was added dropwise to a mixed solution of 5 ml of ethanol, 1 ml of pyridine and 30 ml of benzene at room temperature. The mixture was allowed to stand for 30 minutes, washed with water and dried over Na2SO4, and evaporated under reduced pressure to give 1.3 g of a crude ester. The obtained crude ester was purified by column chromatography on 40 g of silica gel (benzene was used as eluent) to give 0.9 g of 3-phenoxybenzyl 2-(4-carboethoxyphenyl)-2-methylpropyl ether.

Provenance & Evidence