Dimethylformamide → Methyl 4-hydroxy-3-methylbenzoate

To a solution of 4-hydroxy-3-methylbenzoic acid (10.00 g, 65.7 mmol) and DMF (100 μL) in MeOH (35 mL) was added dropwise thionyl chloride (4.8 mL, 65.7 mmol) at room temperature. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with the addition of aqueous saturated sodium bicarbonate solution (50 mL), and methanol was removed under reduced pressure. The residue was extracted with EtOAc (3×50 mL) and dried over sodium sulfate, filtered and concentrated in vacuo to provide methyl 4-hydroxy-3-methyl-benzoate (10.53 g, 96%) as a light brown solid. ESI-MS m/z calc. 166.0. Found 167.1 (M+1)+; Retention time: 1.09 minutes (3 min run).

1. customThe reaction mixture was quenched with the addition of aqueous saturated sodium bicarbonate solution (50 mL), and methanol
2. customwas removed under reduced pressure
3. extractionThe residue was extracted with EtOAc (3×50 mL)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-8517ffd9cd7a44628e87919d27e9d198

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08828996B2