Acetic Anhydride → 4-Nitrophthalic acid anhydride

HRID 1576119Notes

Reaction equation

HRID 1576119 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. temperatureat reflux for 6 hours
  2. customwas removed by distillation at atmospheric pressure
  3. customThe excess acetic anhydride was removed by distillation at 15 mm Hg pressure with the flask temperature not
  4. customexceeding 120°C

Sources & evidence

ORD record
ord-1c358ee00ec1411c959731150046f74d
Source dataset
uspto-grants-1976_09
Patent number
US03979416

Reaction notes

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