Ethanol → 4'-(Hexyloxy)[1,1'-biphenyl]-4-ol

Participants

Reaction Steps

A mixture of 74 g (0.40 moles) of biphenol and 20 g (0.50 moles) of sodium hydroxide in 600 ml of ethanol was refluxed for 1 hour. At reflux temperature 66 g (0.40 moles) of 6-bromohexane were added over a period of 1 hour. The reaction mixture was refluxed for 18 hours and cooled to room temperature, and the precipitate was filtrated. The filtrate was treated with 500 ml of water and the precipitated 4-hexyloxy-4'-hydroxybiphenyl was filtrated and washed with water. After drying 29 g of product were obtained. An additional amount of product was obtained by refluxing the precipitate collected from the reaction mixture with 45 g of potassium hydroxide in 600 ml of ethanol for 3 hours. This mixture was cooled to room temperature and the insoluble dihexyloxybiphenyl filtered off. The clear filtrate was treated with 200 ml of 6N hydrochloric acid and the precipitated 4-hexyloxy-4'-hydroxybiphenyl was filtrated, washed with water, and dried. The yield was 19 g. The total yield was 48 g (44% of theory).

Provenance & Evidence