Lithium hydroxide, monohydrate → (Rs)-(e)-4-[3-(4,4-dimethyl-thiochroman-6-yl)-oct-1-enyl]-benzoic acid

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Reaction Steps

200 mg of (RS)-(E)-methyl 4-[3-(4,4-dimethyl-thiochroman-6-yl)-oct-1-enyl]-benzoate were dissolved in 10 ml THF/3 ml water/3 ml methanol and 200 mg of lithium hydroxide hydrate were added. The mixture was stirred at room temperature 4 hours. The mixture was diluted with 10 ml water and acidified to pH 2 with 1N hydrochloric. The resulting suspension was taken in 50 ml ether and the phases were separated. The aqueous phase was extracted with three portions of 25 ml ether. The combined extracts were dried over MgSO4. The solvent was removed in vacuo and the crude product was purified by flash chromatography (SiO2, 10% methanol/methylene chloride) followed by recrystalization from hexanes, yielding 185 mg of product as white solid. M.p. 146-146.5° C.

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