Sodium Hydroxide → HCID 15462418, compound

Participants

Reaction Steps

To a suspension of trans-2-(3-acetyl-4,6,-dimethoxy-2-hydroxyphenyl)cyclohexyl acetate (IV; 43 g; 0.128 mol) in methanol (460 ml) was added a solution of sodium hydroxide (20%; 154 ml) using the addition funnel and allowed to stir at room temperature for 15 min. The reaction mixture was then heated to 60° C. and the progress of the reaction monitored by TLC (tlc system 10% ethyl acetate-chloroform; anisaldehyde spray; pdt. Rf value 0.3). Complete consumption of the starting material was seen after stirring at 60° C. for 3 hours. The reaction mixture was then cooled in an ice bath and neutralized with 2N HCl. The precipitated solid was filtered and dried at high vacuum (dry solid 32 g). The filtrate was concentrated in-vacuo to remove methanol and extracted with ethyl acetate. The ethyl acetate layer was washed with water, brine and dried over sodium sulphate. It was concentrated and chromatographed over silica gel (eluent 3% ethyl acetate-chloroform) to get 3 g of the title compound. In total, 35 g of the title compound was isolated (yield 93%; mp. 162-64° C.).

Provenance & Evidence