Toluene → HCID 10614463, compound

Participants

Reaction Conditions

Reaction Steps

Combine 4,4'dihydroxybenzophenone (21.4 g, 0.10 mmol) and sodium hydroxide (4.0 g, 0.10 mmol) in water (50 mL). Heat to 80° C. Add toluene (100 mL). Add benzyl chloride (17.3 mL, 0.15 mmol) in toluene/methanol (100 mL/40 mL). Maintain heating at 70° C. to 80° C. After 3 days, cool to ambient temperature and partition the reaction mixture between ethyl acetate and water. Separate the layers and extract the aqueous layer with ethyl acetate. Combine the organic layers and extract with aqueous 1M sodium hydroxide solution and then water. Evaporate the organic layers in vacuo to give a reside. Combine the aqueous layers and allow to stand to give a solid. Collect the solid by filtration, rinse with water, and dry to give a solid. Combine the solid and the residue obtained from evaporation of the organic layers and recrystallize from toluene to give 4-benzyloxy-4'-hydroxybenzophenone: Rf =0.21 (silica gel, 30% ethyl acetate/hexane).

Provenance & Evidence