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A solution of 1M boron tribromide in dichloromethane (15 mL, 15 mmol) was added dropwise to a solution of 2-isopropyl-3-methoxybenzoic acid in dichloromethane. After stirring for 2 hours, the reaction mixture was cooled to 0° C., quenched with water, and the layers were separated. The aqueous layer was extracted with dichloromethane. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. Purification of the residue by silica gel flash chromatography, eluting with dichloromethane/methanol and 1% acetic acid, gave 3-hydroxy-2-isopropylbenzoic acid as a white crystalline solid (1.32 g, 97.5%).

1. customquenched with water
2. customthe layers were separated
3. extractionThe aqueous layer was extracted with dichloromethane
4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
5. concentrationconcentrated in vacuo
6. customPurification of the residue by silica gel flash chromatography
7. washeluting with dichloromethane/methanol and 1% acetic acid