4-Methylbenzaldehyde → HCID 5918629, compound

Participants

Reaction Steps

A solution of p-tolualdehyde (1 mL, 8.48 mmol), 3-methyl-2-butanone (1.81 mL, 16.96 mmol) and barium hydroxide (0.2 g, 1.17 mmol) in ethanol (4 mL) were mixed and the reaction mixture was heated at reflux for 1 hour. After cooling the solution was extracted with ethyl acetate. The organic layer was washed with water and brine, dried (Mg2SO4), filtered and evaporated to give 1.43 g of trans-4-methyl-1-p-tolyl-pent-1-en-3-one (90%) and used without further purification in the next step (step i). 1H NMR (300 MHz; CDCl3): 1.16 (d, J=7.2 Hz, 6 H), 2.35 (s, 3 H), 2.92 (m, 1 H), 6.79 (dd, J=16.0 Hz, 1 H), 7.19 (d, J=7.5 Hz, 1 H), 7.43 (d, J=8.1 Hz, 1 H), 7.28 (d, J=16.2 Hz, 1 H).

Provenance & Evidence