Water → 4-(2,6-Dimethylphenyl)benzyl alcohol

Participants

Reaction Steps

(4-Bromophenyl)methanol (5.00 g, 32 mmol), (2,6-dimethylphenyl)boronic acid (5.77 g, 39 mmol) and sodium carbonate (10.2 g, 96 mmol) were dissolved in toluene-methanol-water (5:1:1, 210 mL) and, after argon substitution, tetrakistriphenylphosphinepalladium (1.85 g, 1.6 mmol) was added. The reaction mixture was heated under reflux overnight under an argon atmosphere. The reaction mixture was cooled, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=7:3) to give the title compound (4.44 g, yield 65%) as a white powder.

Provenance & Evidence