Phenol → 4'-Hydroxy-4-biphenylcarboxylic acid

Participants

Reaction Conditions

Reaction Steps

Next, 18.7 g (0.060 mole) of the 4,4-bis(4-hydroxyphenyl)cyclohexanecarboxylic acid thus obtained, 2.9 g (0.072 mole) of sodium hydroxide, 100.0 g of phenol, and 0.4 g of 5% palladium-carbon catalyst were charged into a 300-ml stainless steel autoclave. After the air within the autoclave was displaced with nitrogen gas, the reaction mixture was heated at 200° C. for 6 hours. After completion of the reaction, the reaction mixture was filtered to separate unreacted phenol therefrom. The filter cake was dissolved in 50 g of a 20% aqueous solution of sodium hydroxide, and the resulting solution was filtered again to recover the catalyst. In order to precipitate the desired product, the filtrate was brought to pH 1 by the addition of diluted hydrochloric acid. The crystals so formed were collected by filtration, washed with water, and then dried to obtain 11.7 g of 4'-hydroxybiphenyl-4-carboxylic acid in the form of white crystals. Liquid-chromatographic analysis revealed that this product had a purity of 93%, and the greater part of the impurities comprised 4-(4'-hydroxyphenyl)cyclohexanecarboxylic acid. On the basis of the amount of 4,4-bis(4-hydroxyphenyl)cyclohexanecarboxylic acid used, the yield of 4'-hydroxybiphenyl-4-carboxylic acid as corrected for its purity was 85%.

Provenance & Evidence