Methyl 4-Formylbenzoate → Methyl 4-(1-hydroxy-3-methylbutyl)benzoate

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Reaction Steps

A solution of 4-formyl-benzoic acid methyl ester (32.4 g, 147 mmol) in anhydrous THF (800 mL) is cooled to 0° C. while stirring under nitrogen. Isobutyl magnesium bromide (2.0M in diethyl ether, 110 mL, 221 mmol) is added slowly over 10 min. The reaction is allowed to stir at 0° C. for 1 h, and then allowed to warm to room temperature. The reaction is monitored by HPLC, and upon complete consumption of the aldehyde, the reaction is quenched carefully with 1N HCl. The reaction is diluted with diethyl ether and water, followed by extraction. The organic layer is washed with water and brine, followed by drying over anhydrous sodium sulfate. The solution is filtered and concentrated, then further purified using flash column chromatography using ethyl acetate/hexanes to provide 12 g (37%) of product.

Provenance & Evidence