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, followed by dropwise adding (+) brominated 2-methylbutyl (prepared from (-) 2-methylbutanol with phosphorus bromide) (530 g), reacting the mixture for 4 hours, distilling off ethanol, adding water (2 l), filtering, collecting insolubles, and treating the insolubles with toluene to remove solubles. This soluble part was recrystallized from ethanol to obtain scaly crystals having a melting point of 80.5° C.; thus it was confirmed to be di-(2-methylbutyloxy)biphenyl. On the other hand, the insoluble part was heated with hydrochloric acid with stirring, followed by cooling, collecting solids and recrystallizing from toluene and further from ethanol to obtain 4'-(2-methylbutyloxy)-4-hydroxybiphenyl having a m.p. of 137.5° C. (125 g).

Provenance & Evidence