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

Participants

Reaction Steps

Sodium borohydride (76 mg, 2 mmol) was added in small portions to a well-stirred solution of 3,4,4',5-tetramethoxybenzophenone (27) (302 mg, 1 mmol) in ethanol (15 mL) at 0° C. in 15 min and the resultant mixture was stirred for 3 h at room temperature. The reaction was quenched by careful addition of glacial acetic acid (1 mL), and the solvents were removed at reduced pressure. The residue was poured into water, and the product was extracted with ether (2×50 mL). The combined ether extracts were washed with saturated NaHCO3 solution, followed by water, and dried (Na2SO4). Evaporation of solvents and crystallization of the residue from EtOAc-hexane gave product 28 as a white crystalline solid (287 mg, 94%); mp 104°-105° C.; 1H NMR (CDCl3, 200 MHz) δ7.29 (d, J=8.7 Hz, 2H), 6.88 (d, J=8.7 Hz, 2H), 6.60 (s, 2H), 5.73 (d, J=3.2 Hz, 1H), 3.82 (s, 9H), 3.80 (s, 3H), 2.32 (d, J=3.2 Hz, 1H); CIMS (isobutane) m/e 305 (MH+, 100). Anal. (C17H20O5) C, H.

Provenance & Evidence