Lithium Hydroxide → 4-(Cyclohexylmethyloxy)-3-nitrobenzoic acid

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Reaction Steps

To a solution of 21-2 (1.38 g, 4.50 mmol) in THF (22.5 ml) cooled in an ice-bath was added 1N lithium hydroxide solution (22.5 ml). The resulting solution was stirred 18 h while warming to ambient temperature. The solution was partially evaporated at reduced pressure, and the remaining aqueous solution was washed with ethyl acetate (20 ml). The aqueous layer was cooled in an ice-bath, stirred rapidly, and concentrated hydrochloric acid (2 ml) was added dropwise, resulting in formation of a precipitate. The mixture was stirred 1 h, the precipitate was collected and dried in vacuo to give product 21-3 as a white solid, mp: 200°-202° C.

Provenance & Evidence