[1,1'-Biphenyl]-3-carboxylic acid, 2'-methoxy-, methyl ester → Methyl 2'-hydroxy-[1,1'-biphenyl]-3-carboxylate

Beteiligte Stoffe

Reaktionsschritte

Part C: In a dry 50 ml flask, methyl 3-(2-methoxyphenyl)benzoate (1.2 g, 4.95 mmol) was dissolved in dichloromethane (10 ml) under nitrogen, and chilled in a dry-ice/2-propanol bath. Boron tribromide dimethyl sulfide complex (20 ml of a 1M solution in methylene chloride) was added slowly drop-wise and the mixture was allowed to come to room temperature, then the mixture was heated at reflux for 30 hours, then mixed with ice-water (100 ml). The organic material was separated, washed with saturated sodium bicarbonate solution (50 ml), water (50 ml), saturated sodium chloride (60 ml) then dried (MgSO4) and concentrated under reduced pressure. The residue was re-esterified by treatment with methanol and catalytic sulfuric acid, and the product subsequently purified by flash chromatography (SiO2, 3:1 hexane/ethyl acetate) which gave 0.95 g (84%) of methyl 3-(2-hydroxyphenyl)benzoate as a clear oil.

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