Hydrochloric Acid → 2-[4-(2-Hydroxycyclohexylidenemethyl)phenyl]propionic acid

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Reaction Steps

2 g of 2-[4-(2-oxocyclohexylidenemethyl)phenyl]propionic acid (which may be prepared as described in United Kingdom Patent Specification No. 2,002,762) and 0.6 g of sodium cyanoborohydride were dissolved in 40 ml of methanol. The pH of the solution was adjusted to a value of 3 by the addition of 6N hydrochloric acid, whilst ice-cooling. The mixture was then heated under reflux for 1 hour, after which a saturated aqueous solution of sodium chloride was added and the mixture was extracted with diethyl ether. The extract was dried and the solvent was then distilled off. The residue was purified by high speed liquid chromatography, to give the desired compound in a crude form. This was recrystallised from a 1:1 by volume mixture of ethyl acetate and hexane, to give 350 mg of the title compound, melting at 135°-136° C.

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