Boron trifluoride → 4,4'-Bis(3,5-dimethyl-4-hydroxybenzoyl)biphenyl

Participants

Reaction Conditions

Reaction Steps

4,4'-Dicarbomethoxybiphenyl (67 g, 0.25 mole) and 2,6-dimethylphenol (61 g, 0.50 mole) were charged to a one-liter Hastalloy C® shaker tube. The tube was cooled and charged with hydrogen fluoride (200 g) and boron trifluoride (75 g). The tube was heated to 50° C. and shaken at 50° C. for 4 hr. It was then cooled and vented, and the contents, an orange solid in an orange solution, were allowed to evaporate in the hood. The orange solid that resulted was stirred in 2 l. of water, warmed, and isolated by filtration of the warm mixture. The precipitate was stirred in 2 l. of water, warmed, and neutralized with sodium bicarbonate. The solid was isolated by filtration of the warm solution, washed with water, and air dried to afford crude 4,4'-bis(3,5-dimethyl-4-hydroxybenzoyl)biphenyl in a yield of 107.6 g (96%), as a salmon-colored powder.

Provenance & Evidence