p-Anisoyl chloride → 2,6-Dimethoxy-4-methylphenyl 4-methoxyphenyl ketone

Participants

Reaction Steps

3,5-Dimethoxy toluene (1.00 g) obtained in Example 44 was dissolved in anhydrous tetrahydrofuran (10 ml), commercially available 2.5 M n-butyllithium-hexane solution (2.90 ml) was added at -45° C. under nitrogen, and the admixture was stirred for 3 hours. Commercially available 4-methoxybenzoyl chloride (1.23 g) was dissolved in tetrahydrofuran (10 ml), and the resulting solution was added slowly to the admixture at -45° C. The reaction mixture was stirred at room temperature for 1 hour and then partitioned between water and chloroform. The chloroform layer was dried with anhydrous magnesium sulfate, the solvent was removed by reduced-pressure distillation, and the resulting residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (5/1) to obtain 384 mg of the title compound (yield: 20%).

Provenance & Evidence