Butyryl chloride → 2-Butyryl-3-hydroxy-4-(4-methoxyphenyl)cyclohex-2-ene-1-one

Participants

Reaction Steps

Triethylamine (11.1 g) was added dropwise to a stirred solution of 4-(4-methoxyphenyl)cyclohexane-1,3-dione (21.8 g) and n-butyryl chloride (17.6 g) in methylene chloride (100 ml) at ambient temperature. After stirring for a further 1 hour, the reaction solution was washed with water, brine and dried over anhydrous magnesium sulphate. The methylene chloride was removed in vacuo to give a mixture of 4-(4-methoxyphenyl)-1-butyryloxycyclohex-1-en-3-one and 6-(4-methoxyphenyl)-1-butyryloxycyclohex-1-ene-3-one. Toluene (150 ml) was added followed by 4-(N,N-dimethylamino) pyridine (0.5 g) and the mixture refluxed for 8 hours. Evaporation of the toluene in vacuo gave a red oil. Purification on a silica gel column using 5% v/v diethyl ether-methylene chloride as eluant gave the title compound (25 g) as an orange oil.

Provenance & Evidence