Methanol → Methyl 3-hydroxy-4-methylbenzoate

3-Hydroxy-4-methylbenzoic acid (7.60 g) was dissolved in methanol (400 mL), and thereto was added sulfuric acid (15.0 g), and the mixture was allowed to stand at room temperature for 10 hours. The reaction solution was concentrated to 150 mL, and diluted with water, and extracted with toluene. The extract was washed with an aqueous sodium hydrogen carbonate solution, and concentrated to give methyl 3-hydroxy-4-methylbenzoate (7.76 g, 94%). This product was dissolved in THF (140 mL), and thereto was added NaH (60% dispersion in oil, 2.22 g), and the mixture was stirred at 50° C. for one hour. To the mixture was added allyl bromide (7.00 g), and the mixture was refluxed for 5 hours. Water was added to the reaction solution, and the mixture was extracted with toluene, dried, filtered, and concentrated. The residue was purified by silica gel column chromatography to give methyl [3-(allyloxy)-4-methyl]benzoate (8.92 g, 93%).

1. concentrationThe reaction solution was concentrated to 150 mL
2. additiondiluted with water
3. extractionextracted with toluene
4. washThe extract was washed with an aqueous sodium hydrogen carbonate solution
5. concentrationconcentrated

ORD record

ord-4eae34a5a9d74c689dc3404588ea749d

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06759429B2