Water → (S)-(+)-4'-(2-Methylbutyl)-[1,1'-biphenyl]-4-ol

Participants

Reaction Steps

A solution of 33 m moles (8.2 g) of boron tribromide in 25 ml of methylene chloride was cooled to -70° C., and a solution of 28 m moles (7.0 g) of 4'-methoxy-4-(2-methylbutyl)biphenyl in 150 ml of methylene chloride was added dropwise thereto. The mixture was returned to room temperature in 8 hours, and then stirred for five hours. After addition of water, the reaction mixture was extracted with methylene chloride, then purified by column chromatography to obtain 4.0 g of 4'-(2-methylbutyl)-4-hydroxybiphenyl. (yield: 60%)

Provenance & Evidence