Sodium Hydroxide → Biphenyl

Participants

Reaction Steps

0.8 g of sodium hydroxide is dissolved in a solution of 5.09 g of 4'-[(S)-3-methylpentyl]-4-biphenylol (EP-A-131373) in 40 ml of ethanol. The solution is treated with 6.26 g of (S)-2-octyl-p-toluenesulfonate and heated to boiling for 6 hours. Subsequently, the solvent is distilled off and the residue is taken up in 100 ml of diethyl ether and 50 ml of 0.5 N hydrochloric acid. The aqueous phase is separated and back-extracted with 50 ml of diethyl ether. The combined organic phase is washed in succession with 50 ml of water, with 30 ml of 3 N sodium hydroxide solution and three times with 50 ml of water each time, then dried over sodium sulfate and concentrated. Crystallization of the residue from ethanol gives 4-[(R)-1-methylheptyloxy]-4'-(S)-3-methylpentyl]biphenyl, m.p. (C-I) 12° C.

Provenance & Evidence