Hydrochloric Acid → 4'-(2-Methylbutoxy)(1,1'-biphenyl)-4-ol

Participants

Reaction Steps

A mixture of 4,4'-dihydroxybiphenyl (500 g), ethanol (7.5 l) and KOH (302 g) was heated under reflux with stirring, and (+) 2-methylbutyl bromide (prepared from (-)2-methylbutanol with phosphorus bromide)(530 g) was dropwise added for 4 hours to react them, followed by distilling off ethanol, adding water (2 l), filtering, collecting an insoluble substance, and treating this insoluble substance with toluene to remove a soluble substance. This soluble part was recrystallized from ethanol to give scaly crystals of m.p. 80.5° C., which was confirmed to be di-(2-methylbutyloxy)-biphenyl. On the other hand, the above insoluble part was heated together with hydrochloric acid with stirring, followed by cooling, collecting the resulting solid substance and recrystallizing it from toluene and then from ethanol to obtain 4'-(2-methylbutyloxy)-4-hydroxybiphenyl of m.p. 137.5° C. (125 g).

Provenance & Evidence