Water → 4-Amino-2,6-dimethylbenzaldehyde

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Reaction Steps

A suspension of the above 2,2,2-trifluoro-N-(4-formyl-3,5-dimethylphenyl)-acetamide was taken up in MeOH (30 mL) and 1N NaOH (30 mL) was stirred at ambient temperature overnight. Water (200 mL) was added and the resulting solid was filtered, washed with water, and dried to give 4-amino-2,6-dimethylbenzaldehyde. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with water, brine, dried with MgSO4, and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (4:1) as eluent to give additional product.

Provenance & Evidence