Acetic Anhydride → 4-Nitrophthalic acid anhydride

HRID 461621Notes

Reaction equation

HRID 461621 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([OH:15])=[O:14])[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=O)([O-:3])=[O:2].C(OC(=O)C)(=O)C>C(O)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:13](=[O:14])[O:15][C:8](=[O:10])[C:7]2=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 691211,2-Benzenedicarboxylic acid, 4-nitro-

Product 1

HCID 2309764-Nitrophthalic acid anhydride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 21.1 g of 4-nitrophthalic acid and 50.0 g of acetic anhydride were heated at reflux for 6 hours, following which the acetic acid was removed by distillation at atmospheric pressure. The excess acetic anhydride was removed by distillation at 15 mm Hg pressure with the flask temperature not exceeding 120° C, leaving a quantitative yield of crude 4-nitrophthalic anhydride, m.p. 114°-116° C. The product was recrystallized from chloroform to afford a 93% yield of product, m.p. 123°-124° C, identical to that of Example 1.

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 6 hours
  3. customwas removed by distillation at atmospheric pressure
  4. customThe excess acetic anhydride was removed by distillation at 15 mm Hg pressure with the flask temperature not
  5. customexceeding 120° C

Sources & evidence

ORD record
ord-1d0a4b4cae294c89985cacd360cf72fc
Source dataset
uspto-grants-1977_12
Patent number
US04064113

Reaction notes

Loading…