Water → 2-Methoxy-4-(methoxycarbonyl)benzoic acid

To a stirred solution of 4-formyl-3-methoxy-benzoic acid methyl ester (5.0 g, 26 mmol) in tert-butyl alcohol (200 mL) was added NaH2PO4-2H2O (3.6 g, 26 mmol), water (50 mL), 2-methyl-2-butene (11 mL, 104 mmol), and finally NaClO2 (7.02 g, 78 mmol). The reaction was allowed to stir at room temperature for 4 hours. The solvent was then removed under reduced pressure. The crude reaction mixture was then dissolved in DCM (200 mL) and the product was extracted with 1N NaOH (200 mL). The aqueous layer was washed with DCM (200 mL) and then neutralized with 6N HCl (˜40 mL) and the product extracted with DCM (200 mL). The organic layer was then washed with water (100 mL), NaCl (sat.) (100 mL), dried over MgSO4 and then filtered. The solvent was removed under reduced pressure. The crude material was sufficiently pure to use without further purification. The product, 2-methoxyterephthalic acid 4-methyl ester, was obtained in 47% yield (2.4 g, 12.3 mmol).

1. customThe solvent was then removed under reduced pressure
2. customThe crude reaction mixture
3. extractionthe product was extracted with 1N NaOH (200 mL)
4. washThe aqueous layer was washed with DCM (200 mL)
5. extractionthe product extracted with DCM (200 mL)
6. washThe organic layer was then washed with water (100 mL), NaCl (sat.) (100 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. customThe solvent was removed under reduced pressure
10. customto use without further purification

ORD record

ord-4565e35503374aa8adae6ca1fc42365b

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07585879B2