Hydrochloric Acid → 4-(2-Methoxyphenyl)-3-methylbenzoic acid

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Reaction Steps

The (2-methyl-2′-methoxy-[1,1′-biphenyl]-4yl)carboxylic acid methyl ester of Step A (1.9 g, 7.4 mmol) was dissolved in tetrahydrofuran (30 mL) and 1 N sodium hydroxide (15 mL, 15 mmol) was added. The reaction mixture was heated at reflux overnight, then cooled and acidified with 2 N hydrochloric acid. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 1.6 g of product as a white solid, m.p. 160-162° C. MS [(−) APCI, m/z]: 241 [M−H]−. Anal. Calcd. for C15H14O3: C, 74.36; H, 5.82. Found: C, 73.93; H, 5.71.

Provenance & Evidence