Benzene → 4-Bromobutyric acid

Participants

Reaction Conditions

Reaction Steps

In this Example, 14.2 g of 4-bromobutyric acid (85 mmol) was dissolved in 10 g of benzene (128mmol) and, after the temperature was raised to 60° C., 11.9 g of thionyl chloride (100 mmol) was dropwise added. Thereafter, the temperature was raised to 65 to 75° C. and the mixture was stirred at that temperature for one hour. Then, after the mixture was cooled to 20° C., the reaction solution was dropwise added into a suspension solution of 30 g of benzene (256 mmol) and 12 g of aluminum chloride (90 mmol) at 10° C. After stirring the mixture at that temperature for one hour, the temperature was raised to 20° C. and the mixture was further stirred for 30 minutes and added into a 10% aqueous solution of hydrochloric acid that had been cooled to 10° C. Then, the aqueous phase was extracted with benzene, and the organic phase was washed with diluted hydrochloric acid, an aqueous solution of sodium hydrogencarbonate, an aqueous solution of sodium hydroxide, and brine, followed by removing the solvent by distillation under reduced pressure to give 4-bromobutyrophenone in a 62.0% yield from 4-bromobutyric acid.

Provenance & Evidence