Alpha-Methylstyrene → 4,4'-Dihydroxybiphenyl

Participants

Reaction Steps

A 300-ml stainless steel autoclave was charged with 38.0 g (0.20 mole) of 4-(4-hydroxyphenyl)-3-cyclohexene-1-ol, 1.5 g of 5% palladium-carbon, 70.9 g (0.60 mole) of α-methylstyrene and 100 g of water, and the internal atmosphere was replaced with nitrogen. The mixture was heated and reacted at 200° C. for 3 hours. The reaction mass was poured into a large volume of an aqueous sodium hydroxide solution, and the insoluble catalyst was removed by filtration. The organic layer was removed from the filtrate. The rest of the filtrate was neutralized to pH 4 by adding an aqueous hydrochloric acid solution. The separated crystals were filtered, washed with water and dried to obtain 37.0 g of 4,4'-biphenol as white crystals. The product had a purity of 98.0% and the yield was 97.4% based on 4-(4-hydroxyphenyl)-3-cyclohexene-1-ol.

Provenance & Evidence