4-Hydroxybiphenyl → HCID 53649217, compound

Participants

Reaction Steps

A mixture in acetone of 4-phenylphenol (0.85 g, 5.0 mmol) and potassium carbonate (0.76 g, 5.5 mmol) was stirred for 30 minutes. Neat methyl 5-bromovalerate (0.78 mL, 5.5 mmol) was added dropwise via syringe and the reaction mixture was stirred for 2 hours at ambient temperature and overnight at reflux. Catalytic KI was then added and the reaction mixture was heated overnight at reflux. An additional 10 drops of methyl 5-bromovalerate was then added and reflux was continued for 8 hours. The reaction mixture was cooled to ambient temperature and filtered. The collected solid was washed with acetone and the combined filtrate and washings were concentrated in vacuo. The residue was partitioned between ethyl ether and water. The aqueous phase was extracted with ethyl ether. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give 5-(4-phenylphenoxy)pentanoic acid methyl ester (1.66 g) as a white powder.

Provenance & Evidence