Methanol → (3-Chloro-4-hydroxy-5-methyl-phenyl)-acetic acid methyl ester

Temperature

70 °C

A solution of (3-chloro-4-hydroxy-5-methyl-phenyl)-acetic acid (5b) (1.4 g, 6.98 mmol) in methanol (60 mL) was treated with concentrated sulfuric acid (0.5 mL) at room temperature under argon. The reaction mixture was heated to 70° C. for 24 h. At this time, the reaction mixture was concentrated under vacuum. The resulting oil was diluted with ethyl acetate (100 mL). The organics were washed with water (2×50 mL), dried with magnesium sulfate, filtered and concentrated. The resulting residue was purified by column chromatography using silica gel eluted with 10% ethyl acetate in petroleum ether to afford 3-chloro-4-hydroxy-5-methyl-phenyl)-acetic acid methyl ester (6b) (1.36 g, 91%) as a white solid; EI(+)-HRMS m/z calcd for C10H11ClO3 (M+) 214.0397, found 214.0400. Molecular Weight=214.6504; Exact Mass=214.0397

1. concentrationAt this time, the reaction mixture was concentrated under vacuum
2. additionThe resulting oil was diluted with ethyl acetate (100 mL)
3. washThe organics were washed with water (2×50 mL)
4. dry with materialdried with magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe resulting residue was purified by column chromatography
8. washeluted with 10% ethyl acetate in petroleum ether

ORD record

ord-34ebab68b3b648cdba77cc3e57530762

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07807674B2