Water → HCID 19899117, compound

Participants

Reaction Conditions

Reaction Steps

3 g (0.0094 mol) of a mixture of methyl 3-(4-chlorophenyl)-4,5,6,7,8,9-hexahydrocyclooct[d]isoxazole-6-carboxylate and methyl 3-(4-chlorophenyl)-4,5,6,7,8,9-hexahydrocyclooct[d]isoxazole-7-carboxylate were dissolved in 75 ml of methanol. 1.5 g of potassium hydroxide and 7 ml of water were added and the mixture was stirred at 20° C. for 18 hours. The methanol was removed by evaporation and an excess of water was added. The mixture was extracted twice with ethyl acetate and the aqueous phase was acidified with 2N hydrochloric acid. The aqueous-acidic layer was extracted three times with ethyl acetate and the combined ethyl acetate extracts were washed with sodium chloride solution and dried over magnesium sulfate. After evaporation and several crystallizations of the residue from ethyl acetate/hexane, there was obtained 0.78 g of 3-(4-chlorophenyl)-4,5,6,7,8,9-hexahydrocyclooct[d]isoxazole-7-carboxylic acid of melting point 147°-150° C.

Provenance & Evidence