Hydrochloric Acid → HCID 14086163, compound

Participants

Reaction Steps

To a mixture of 4-(4-phenylbutyl)phenyl acetate (8.29 g) in methanol (112 ml) and water (97 ml) was added sodium carbonate (13.10 g). The reaction was refluxed. After 3.5 hours, the reaction mixture was allowed to cool to room temperature. After 25 minutes at room temperature, the reaction mixture was treated with 5N HCl (50 ml). It was then concentrated in vacuo to remove the majority of the methanol present. Diethyl ether (250 ml) was added to the residue, then the material was treated with 1N HCl (3×100 ml) and the phases were separated. The material was dissolved in diethyl ether, then the denied compound was isolated by flash silica-gel filtration, eluting with hexane/ethyl acetate (20:1, 92×13 ml). The fractions containing the denied compound were combined and concentrated in vacuo to give 1.57 g of 4-(4-phenyl butyl)phenol an oil. Upon standing at room temperature the oil crystallized out.

Provenance & Evidence