Hydrochloric Acid → 5-Acetyl-2-{[2-(chloromethyl)-2-propenyl]oxy}benzaldehyde

Participants

Reaction Steps

6.02 g (16.31 mmol) of tetrabutylammonium iodide, 6.17 g (2.5 equivalents) of sodium carbonate and, finally, 6.7 ml (58.2 mmol) of 2-chloromethyl-3-chloro-1-propene are successively added to 3.82 g (23 mmol) of 5-acetyl-2-hydroxybenzaldehyde, prepared according to Tromelin, A. et al., Synthesis, (1985), 1074–1076, and then Laali, K. et al., Journal of Organic Chemistry, 58, (1993), 1385–1392, in solution in 250 ml of N,N-dimethylformamide. The medium is stirred for 21 hours. After addition of water and 1N hydrochloric acid, the solution is extracted with dichloromethane. The organic phase is subsequently washed, then dried and, finally, concentrated under vacuum. The crude reaction product is purified by chromatography on silica gel (ethyl acetate/heptane 20/80) to give 3.06 g (52%) of 5-acetyl-2-{[2-(chloromethyl)-2-propenyl]oxy}benzaldehyde in the form of a yellow-white solid; 1H NMR (300 MHz, CDCl3): 10.49 (s, 1H), 8.38 (d, J=2.1 Hz, 1H), 8.18 (dd, J=2.1 Hz and 8.7 Hz, 1H), 7.08 (d, J=8.7 Hz, 1H), 5.46 and 5.41 (2s, 2H), 4.83 (s, 2H), 4.21 (s, 2H), 2.58 (s, 3H).

Provenance & Evidence