Nitric Acid → 5,6-Dimethoxy-4-nitro-isobenzofuran-1,3-dione

HRID 1881208

Reaction equation

HRID 1881208 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:14]([OH:16])=[O:15])[C:6](=[CH:10][C:11]=1[O:12][CH3:13])[C:7]([OH:9])=O.S(=O)(=O)(O)O.[N+:22]([O-])([OH:24])=[O:23]>[Cl-].[Na+].O>[CH3:13][O:12][C:11]1[C:10]([N+:22]([O-:24])=[O:23])=[C:6]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[C:14](=[O:15])[O:16][C:7]2=[O:9]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 2909884,5-Dimethoxyphthalic acid

Product 1

HCID 866334445,6-Dimethoxy-4-nitro-isobenzofuran-1,3-dione

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

4,5-Dimethoxy-phthalic acid (1.0 g) was cooled in ice-water bath. A cooled mixture of sulfuric acid (3.0 ml) and fuming nitric acid (3.0 ml) was added dropwise. The mixture was stirred for 10 minutes and left standing for 10 minutes. A mixture of brine and ice was added (1:1). The solid was filtered off, washed with water and recrystallized from ethanol.

Workup

  1. additionwas added dropwise
  2. waitleft
  3. waitstanding for 10 minutes
  4. additionwas added (1:1)
  5. filtrationThe solid was filtered off
  6. washwashed with water
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a8ab32bee61b4f17bd04c7c544c2be13
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Linked notes

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