Lithium Hydroxide → (E)-2-[2-(3-chlorophenyl)vinyl]-5-methoxybenzoic acid

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Reaction Steps

Crude 2-[(E)-2-(3-chlorophenyl)vinyl]-5-methoxybenzoic acid methyl ester was suspended in methanol:THF:water (3:1:1 [v/v], 400 mL) and lithium hydroxide (12.10 g, 289 mmol) added. The mixture was stirred for 22 h at ambient temperature and concentrated in vacuo to give a pale brown solid. The crude product was re-dissolved in water (400 mL), the solution washed with diethyl ether (3×250 mL) and acidified to pH 2 with 1 N HCl (aq.). The aqueous was extracted with ethyl acetate (3×200 mL), the organic phase dried (MgSO4) and concentrated in vacuo to give a tan solid which was triturated with methanol and filtered to give (E)-2-[2-(3-chlorophenyl)vinyl]-5-methoxybenzoic acid (15.43 g, 53.44 mmol, 74% for 2 steps from 2-bromo-5-methoxybenzoic acid methyl ester) as an off-white powder.

Provenance & Evidence