Hydrochloric Acid → HCID 178450140, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of aluminum trichloride (4.0 g, 0.03 mole) in dichloromethane (20 ml) at 0° C. was added 3-hydroxy-5-mesityl-2-propionylcyclohex-2-en-1-one (2.9, 0.01 mole) in dichloromethane (10 ml). The mixture was stirred at 0° C. for five minutes and then crotonyl chloride (1.1 g, 0.01 mole) was added. Stirring was continued at 0° C. for 30 minutes and then at 20° C. for 3 hours. The brown solution was poured into cold dilute hydrochloric acid (2M, 200 ml) and shaken occasionally as it was allowed to warm to room temperature. The organic phase was separated and the aqueous phase was shaken with chloroform (2×100 ml). The combined organic extracts were dried over magnesium sulphate and evaporated to give 3-hydroxy-5-(3-crotonyl-2,4,6-trimethylphenyl)-2-propionylcyclohex-2-en-1-one (4.1 g, 83%) as a pale brown oil. Proton magnetic resonance spectrum (CDCl3 ; δ in ppm): 1.16 (3H, t); 1.93 (3H, d, J=7 Hz); 2.07 (3H, s); 2.17 (3H, s); 2.38 (3H, s); 2.2-4.0 (7H, m); 6.1-6.8 (2H, m); 6.86 (1H, s); 18.20 (1H, s).

Provenance & Evidence