Acetone → Benzaldehyde, 4-(phenylmethoxy)-

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-hydroxybenzaldehyde (1) (3.05 g, 25.00 mmol), benzyl bromide (4.4 g, 25.75 mmol), and K2CO3 (4.25 g, 30.75 mmol) in acetone (75 mL) is stirred at 65° C. under argon for 19.5 h, then cooled to room temperature, and concentrated at reduced pressure to remove the acetone. The residue is diluted with 2 N HCl (60 mL) and extracted with ethyl acetate (80 mL and 50 mL). The extract is washed (brine) and dried. After solvent removal at reduced pressure, the residue is purified on silica gel (16.7% ethyl acetate/hexane) to give 4.56 g (86%) of 2 as a white solid, mp 70-72° C. IR 2943, 1738, 1484, 1230 cm−1; 1H NMR (CDCl3) δ 5.19 (s, 2H, CH2), 7.11 (d, J=8.7 Hz, 2H, 3,5-ArH), 7.36-7.49 (m, 5H, PhH), 7.87 (d, J=8.7 Hz, 2H, 2,6-ArH), 9.92 ppm (s, 1H, CHO).

Provenance & Evidence