Sodium Hydroxide → p-[(1RS, 2RS)-1-(10-hexylthiodecyl)-6-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]benzoic acid

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Reaction Steps

Aqueous 2N-sodium hydroxide solution (10 ml.) was added to a solution of p-[(1RS, 2RS)-1-(10-hexylthiodecyl)-6-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-N,N-dimethylbenzamide (Example 7; 0.24 g.) in ethanol (10 ml.) and the mixture was heated under reflux for 16 hours. The ethanol was removed by evaporation and the residue was acidified to pH 1 with aqueous 2N-hydrochloric acid and extracted three times with ethyl acetate (15 ml. each time). The combined extracts were washed with water, dried and evaporated to dryness and the residue was purified by chromatography on a silica gel column using a 4:1 v/v mixture of toluene and ethyl acetate as eluent. There was thus obtained as an oil p-[(1RS, 2RS)-1-(10-hexylthiodecyl)-6-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]benzoic acid, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Provenance & Evidence