Hydrochloric Acid → 3,5-Dimethoxy-4-methylphenol

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Reaction Steps

To a solution of 3,5-dimethoxy-4-methylphenyl formate (2.9 g, 14.8 mmol) in wet MeOH (81 mL) was added K2CO3 (8.1 g, 58.6 mmol). The mixture was stirred for 2 hrs at room temperature then H2O (2-3 mL) was added. After stirring for 21 hrs, the mixture was diluted with H2O, acidified with 6M HCl to pH 3-4, and extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (0-35% EtOAc-hexanes) gave 3,5-dimethoxy-4-methylphenol as an impure yellow powder (0.71 g, 29% yield).

Provenance & Evidence