Acetic Anhydride → 3-Acetoxy-4-nitrobenzoic acid

HRID 2260100Notes

Reaction equation

HRID 2260100 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].[C:14](OC(=O)C)(=[O:16])[CH3:15]>N1C=CC=CC=1>[C:14]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6])(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 692653-Hydroxy-4-nitrobenzoic acid

Product 1

HCID 181880843-Acetoxy-4-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-hydroxy-4-nitrobenzoic acid (10g, 55 mmole) in acetic anhydride (20 ml) and anhydrous pyridine (20 ml) was refluxed for 4 hours. The reaction mixture was poured onto ice and the resulting mixture was extracted with ethyl acetate (2×100 ml). The organic layer was washed successively with dilute HCl solution (2×100 ml) and saturated brine solution, dried over Na2SO4, filtered and evaporated to give 3-acetoxy-4-nitrobenzoic acid.

Workup

  1. temperaturewas refluxed for 4 hours
  2. additionThe reaction mixture was poured onto ice
  3. extractionthe resulting mixture was extracted with ethyl acetate (2×100 ml)
  4. washThe organic layer was washed successively with dilute HCl solution (2×100 ml) and saturated brine solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a3240ca05c8c4bdd90f70cc1a94a6d7c
Source dataset
uspto-grants-1995_12
Patent number
US05476849

Reaction notes

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