Benzyl Bromide → 4-Benzyloxy-3-ethyl-5-methylbenzaldehyde

Participants

Reaction Conditions

Reaction Steps

Potassium carbonate (4.38 g, 32 mmol) is added to a stirred solution of 3-ethyl-4-hydroxy-5-methyl-benzaldehyde (2.6 g, 16 mmol) in acetone (70 mL). Benzylbromide (2.07 mL, 17 mmol) is then added dropwise and the reaction mixture is heated to 60° C. for 3 h. The suspension is filtered, the filtrate is evaporated and the crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 4-benzyloxy-3-ethyl-5-methyl-benzaldehyde (3.66 g) as a colorless oil; 1H NMR (CDCl3): δ 1.28 (t, J=7.5 Hz, 3H), 2.40 (s, 3H), 2.76 (q, J=7.5 Hz, 2H), 4.90 (s, 2H), 7.50-7.35 (m, 5H), 7.62 (s, 1H), 7.65 (s, 1H), 9.94 (s, 1H).

Provenance & Evidence