Anisole → (4-Methoxyphenyl)(3,4,5-trimethoxyphenyl)methanone

Participants

Reaction Steps

Anhydrous AlCl3 (260 mg, 2 mmol) was added to a well-stirred solution of 3,4,5-trimethoxybenzoyl chloride (25) (461 mg, 2 mmol) and anisole (216 mg, 2 mmol) at 0° C. in CH2Cl2 (25 mL). The mixture was stirred while allowing it to warm to room temperature. After 6 h, the resultant dark reaction mixture was poured into ice cold 5% HCl (20 mL), and the CH2Cl2 layer was separated. The aqueous layer was extracted with an additional 30 mL of CH2Cl2, and the combined CH2Cl2 solutions were washed with saturated sodium bicarbonate solution. Evaporation of solvents from the dried CH2Cl2 extract and purification of the residue by chromatography on a column of silica gel, using 5% EtOAc in hexane as eluent, gave product 27 (487 mg, 80%); mp 72°-73° C.; 1H NMR (CDCl3, 200 MHz) δ7.83 (d, J=8.7 Hz, 2H), 7.03 (s, 2H), 6.98 (d, J=8.7 Hz, 2H), 3.94 (s, 3H), 3.90 (s, 3H), 3.88 (s, 6H); CIMS (isobutane) m/e 303 (MH+, 100). Anal. (C17H18O5), C, H.

Provenance & Evidence