Benzyl Alcohol → HCID 18433379, compound

Temperature

50 °C

Sodium hydride (918 mg, 23.0 mmol) was added to benzyl alcohol (30 ml) in portions. After vigorous evolution of a hydrogen gas stopped, a solution of 3-fluoro-5-methoxy-4-nitrophenylacetic acid (2.63 g, 11.5 mmol) in benzyl alcohol (20 ml) was added to the reaction mixture. After stirring at 50° C. for 15 hours, the reaction mixture was cooled. To the mixture was added 1N NaOH (100 ml), followed by extraction with ether (200 ml). After addition of 1N HCl to the water layer, the mixture was extracted with ether (2×200 ml). The extract was dried over anhydrous magnesium sulfate and then, distilled under reduced pressure to remove the solvent, whereby a pale yellow oil was obtained. Methanol (50 ml) and concentrated sulfuric acid (0.5 ml) were added to the resulting oil and the mixture was heated and refluxed for 4 hours under stirring. The reaction mixture was then cooled to room temperature. After addition of a saturated aqueous solution of sodium bicarbonate for neutralization, the mixture was extracted with chloroform (2×250 ml). The extract was dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from chloroform eluate solutions, the title compound (2.77 g, 61%) was obtained as a yellow oil.

1. temperaturethe reaction mixture was cooled
2. extractionfollowed by extraction with ether (200 ml)
3. additionAfter addition of 1N HCl to the water layer
4. extractionthe mixture was extracted with ether (2×200 ml)
5. dry with materialThe extract was dried over anhydrous magnesium sulfate
6. distillationdistilled under reduced pressure
7. customto remove the solvent, whereby a pale yellow oil
8. customwas obtained
9. temperaturethe mixture was heated
10. temperaturerefluxed for 4 hours
11. stirringunder stirring
12. temperatureThe reaction mixture was then cooled to room temperature
13. extractionthe mixture was extracted with chloroform (2×250 ml)
14. dry with materialThe extract was dried over anhydrous magnesium sulfate
15. distillationdistilled under reduced pressure
16. customto remove the solvent
17. customThe residue was purified by chromatography on a silica gel column, whereby from chloroform eluate solutions

ORD record

ord-4c031ac0f79f4c98a8202ad7994bcc4c

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07157487B2