Methyl 4-amino-o-anisate → Methyl 4-hydroxy-2-methoxybenzoate

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Reaction Steps

4-Amino-2-methoxy benzoic acid methyl ester (15 g, 82.7 mmol) was dissolved in sulfuric acid (80 ml of a 25% solution). The solution was cooled in an ice bath and diazotized with saturated sodium nitrite solution (8.57 g, 124 mmol) maintaining the temperature below 5° C. The diazonium solution was poured slowly into boiling sulphuric acid (1L of a 3% solution) and the mixture was heated for an additional 5 mins. The mixture was then allowed to cool before being extracted with dichloromethane. The organic extracts were combined, dried over sodium sulfate and concentrated in vacuo to afford a brown solid (9.7 g).

Provenance & Evidence