Methanol → Methyl 3-chloro-4-hydroxyphenylacetate

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Reaction Steps

2-(3-Chloro-4-hydroxyphenyl)acetic acid (5.0 g, 26.8 mmol) was dissolved in 30 mL of MeOH and H2SO4 (0.744 ml, 13.4 mmol) was added dropwise at ambient temperature. The reaction was refluxed for four hours and then concentrated in vacuo. The residue was diluted with 150 mL of EtOAc and washed sequentially with saturated NaHCO3, water, and brine, dried over H2SO4, and concentrated in vacuo to provide methyl 2-(3-chloro-4-hydroxyphenyl)acetate (5.16 g, 96.0% yield) as a semi-opaque thick oil.

Provenance & Evidence