Water → Butanoic acid, 4-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-

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Reaction Steps

To a solution of 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (3.57 g, 15 mmole) and ethyl 4-bromobutyrate (3.23 g, 16.5 mmole) in 10 ml of acetone was added potassium hydroxide flakes (2.52 g, 45 mmole) Water (20 ml) was added and the solution was stirred for 1.5 hours, then concentrated in vacuo to dryness. Water (50 ml) was added to the residue and the aqueous mixture was washed with three portions (75 ml each) of ethyl acetate. The aqueous layer was separated and acidified with concentrated hydrochloric acid and extracted with two portions (50 ml each) of ethyl acetate. The organic layers were combined and washed with water, dried over sodium sulfate, filtered and concentrated in vacuo to an oil. Purification by chromatography on silica gel and recrystallization from diethyl ether-hexane yielded, after collection and drying in vacuo, the title compound, m.p. 112°-113.5°.

Provenance & Evidence