Nitric Acid → 2-Hydroxy-5-nitrobenzene-1,3-dicarboxylic acid

HRID 1112607Notes

Reaction equation

HRID 1112607 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[OH:10][C:11]1[C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]>C(O)(=O)C.O>[N+:6]([C:17]1[CH:16]=[C:12]([C:13]([OH:15])=[O:14])[C:11]([OH:10])=[C:19]([CH:18]=1)[C:20]([OH:22])=[O:21])([O-:9])=[O:7]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 118121,3-Benzenedicarboxylic acid, 2-hydroxy- (9CI)

Product 1

HCID 128964322-Hydroxy-5-nitrobenzene-1,3-dicarboxylic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent3×HCID 962WaterSolvent

Procedure

A mixture of 40 ml of sulfuric acid and 33 ml of nitric acid is stirred for 10 minutes and then 10 ml of acetic acid is added. To this is added a suspension of 10 g of 2-hydroxyisophthalic acid (Org. Syn., Vol. 5, p. 617) in 20 ml of acetic acid slowly with cooling in a water bath. A 10 ml portion of acetic acid is added. The reaction mixture is dissolved in water and extracted with ether. The ether is washed with saturated saline, dried over sodium sulfate and evaporated giving 5-nitro-2-hydroxyisophthalic acid as an orange oil.

Workup

  1. additionTo this is added
  2. temperaturewith cooling in a water bath
  3. extractionextracted with ether
  4. washThe ether is washed with saturated saline
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-9dd9740cc0884828bd29623092c19782
Source dataset
uspto-grants-1978_10
Patent number
US04123455

Reaction notes

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