Sodium Hydroxide → 2-Methoxy-6-methylbenzoic acid

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Reaction Steps

Ethyl-2-methoxy-6-methylbenzoate (30.4 g, 0.157 mol) was added to 100 mL 3.2 M NaOH (2 equiv) and 150 mL hot EtOH. The mixture was refluxed overnight after which EtOH was removed in vacuo. The aqueous mixture was acidified with 5 M HCl to pH 3. CH2Cl2 (200 mL) was added, and the layers were separated. The water layer was extracted two times with 200 mL CH2Cl2, and the organic layers were combined and dried over Na2SO4. Filtering the Na2SO4 and concentrating the CH2Cl2 to dryness yielded 21.4 g (0.129 mol, 82.3%) of 2-methoxy-6-methyl-benzoic acid.

Provenance & Evidence