Acetic Anhydride → HCID 54559907, compound

A mixture of 5-hydroxy-2-nitrobenzaldehyde (4 g.) and acetic anhydride (10 ml.) was heated on a steam bath for 1 hour, then poured into water (100 ml.) and extracted with diethyl ether (3×50 ml.). The extracts were combined and dried, and the solvent was evaporated. The residue of 5-acetoxy-2-nitrobenzaldehyde was dissolved in absolute ethanol (100 ml.), and stirred and ice-cooled while sodium borohydride (1.5 g.) was added in portions. The reaction mixture was stirred at room temperature for 1 hour, then water (100 ml.) was added, and the mixture was extracted with ether (3×70 ml.). The extracts were combined and dried, and the solvent was evaporated to give 5-acetoxy-2-nitrobenzyl alcohol, which was hydrogenated by the general process described in the latter part of Example 13(a) to give the required starting material.

1. temperaturewas heated on a steam bath for 1 hour
2. extractionextracted with diethyl ether (3×50 ml.)
3. customdried
4. customthe solvent was evaporated
5. dissolutionThe residue of 5-acetoxy-2-nitrobenzaldehyde was dissolved in absolute ethanol (100 ml.)
6. temperatureice-cooled while sodium borohydride (1.5 g.)
7. additionwas added in portions
8. stirringThe reaction mixture was stirred at room temperature for 1 hour
9. additionwater (100 ml.) was added
10. extractionthe mixture was extracted with ether (3×70 ml.)
11. customdried
12. customthe solvent was evaporated

ORD record

ord-de71f879cc154ade8b3b41a92f376b3d

Source dataset

uspto-grants-1981_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04268510