Methanol → HCID 18433366, compound

To 3-hydroxy-4-nitrophenylacetic acid (5.45 g, 27.6 mol) and methanol (100 ml) was added concentrated sulfuric acid (0.5 ml). The mixture was then heated under reflux for 4 hours under stirring. After cooling to room temperature, the reaction mixture was distilled under reduced pressure to remove the solvent. Water (100 ml) was added to the residue, followed by extraction with ether (300 ml). The extract was washed successively with a saturated aqueous solution (100 ml) of sodium bicarbonate and saturated brine (100 ml), dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, whereby the title compound (4.90 g, 84%) was obtained as a yellow crystalline powder.

1. temperatureThe mixture was then heated
2. temperatureunder reflux for 4 hours
3. distillationthe reaction mixture was distilled under reduced pressure
4. customto remove the solvent
5. additionWater (100 ml) was added to the residue
6. extractionfollowed by extraction with ether (300 ml)
7. washThe extract was washed successively with a saturated aqueous solution (100 ml) of sodium bicarbonate and saturated brine (100 ml)
8. dry with materialdried over anhydrous magnesium sulfate
9. distillationdistilled under reduced pressure
10. customto remove the solvent, whereby the title compound (4.90 g, 84%)
11. customwas obtained as a yellow crystalline powder

ORD record

ord-c0881b3724bb42cbab29c72d617c7511

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07157487B2