Hydrochloric Acid → Benzoic acid, 3-(1,1-dimethylethyl)-4-methoxy-

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Reaction Steps

Preparation C11, Step 2: Methyl 3-tert-butyl-4-methoxybenzoate (1.12 g, 5.03 mmol, 1 eq) was dissolved in 1N NaOH in methanol (50.38 mL, 50.3 mmol, 10 eq) at room temperature then refluxed for 4 hours. Worked up stripping off the methanol. Added H2O (10 mL) then adjusted the pH to 3 with 6N HCl. Solids precipitated. Extracted the suspension 3 times with methylene chloride (20 mL). The organic layers were combined, dried (sodium sulfate) and stripped to give 3-tert-butyl-4-methoxybenzoic acid (0.98 g) as a white solid. Yield=93%. LCMS detects (M+H)+=208.25.

Provenance & Evidence