(2-Butylbenzofuran-3-yl) (4-hydroxyphenyl) ketone → 4-[(2-Butyl-benzofuran-3-yl)-hydroxy-methyl]-phenol

Participants

Reaction Conditions

Reaction Steps

A solution containing commercial 2-n-butyl-3-(4-hydroxybenzoyl)benzofuran (0.500 g, 17.0 mmol) and lithium aluminum hydride (34.0 mmol) in THF (84 mL) was refluxed for 3 h. The reaction was cooled to -10° C., and carefully quenched with 0.1N NaOH and H2O. The aqueous solution was extracted with ether and concentrated. Purification on silica gel gave the title compound as a white solid, mp 94-96° C. (DMSO-d6) δ 0.90 (t, 3 H), 1.35 (sextet, 2 H), 1.64 (quintet, 2 H), 2.84 (t, 2 H), 5.67 (d, 1 H), 5.87 (d, 1 H), 6.69 (d, 2 H), 7.07 (t, 1 H), 7.15 (dt, 1 H), 7.22 (d, 2 H), 7.40-7.43 (m, 2 H), 9.24 (s, 1 H). IR (KBr) 3350, 2950, 1610, 1510 and 1450 cm-1. mass spectrum (EI) m/z 296 (M+). Anal. Calcd. for C19H20O3 : C, 77.00; H, 6.80; N, 0.00. Found: C, 75.63; H, 6.86; N, 0.04.

Provenance & Evidence