Benzoyl chloride → 3-Benzoyloxy-2-[1-(ethoxyimino)propyl]-5-mesitylcyclohex-2-en-1-one

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Reaction Steps

A solution of sodium hydroxide (0.12 g) in water (0.7 ml) was added dropwise, with stirring, to a solution of 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-mesitylcyclohex-2-en-1-one (0.89 g) in tetrahydrofuran (9.5 ml). Benzoyl chloride (0.42 g) was added dropwise, with stirring and the mixture was stirred at room temperature for a period of 30 minutes. The solvent was removed by evaporation under reduced pressure and the residue was taken up in dichloromethane and water. The dichloromethane solution was separated, washed twice with water, dried, and the solvent evaporated under reduced pressure. The remaining oil was triturated with petroleum ether (b.p. 40°-60° C.) and the solid which formed was recrystallised from isopropanol to give 3-benzoyloxy-2-[1-(ethoxyimino)propyl]-5-mesitylcyclohex-2-en-1-one (0.79 g) as a solid m.p. 94°-95.5° C.

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