6-Nitro-1,3-benzodioxole-5-carboxaldehyde → 6-Nitro-1,3-benzodioxole-5-carboxylic acid

HRID 1249741Notes

Reaction equation

HRID 1249741 reaction equation
[CH2:1]1[O:11][C:10]2[CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]([CH:6]=[O:7])=[CH:4][C:3]=2[O:2]1.[Mn]([O-])(=O)(=O)=[O:16].[K+]>O.CC(C)=O>[N+:12]([C:8]1[C:5]([C:6]([OH:16])=[O:7])=[CH:4][C:3]2[O:2][CH2:1][O:11][C:10]=2[CH:9]=1)([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 128406-Nitro-1,3-benzodioxole-5-carboxaldehydeHCID 516875Potassium Permanganate

Product 1

HCID 2464356-Nitro-1,3-benzodioxole-5-carboxylic acidYield 73.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixture of 3,4-(methylenedioxy)-6-nitrobenzaldehyde (25 g, 128 mmol) and potassium permanganate (40 g, 253 mmol) in a mixture of 300 mL water and 200 mL acetone was stirred overnight at ambient temperature and then heated to 100° C. for 1 hour. The reaction mixture was filtered through Celite®, acetone was removed in vacuo, and the product precipitated from the water solution by acidification to pH 1.2 with concentrated hydrochloric acid to give 6-nitro-benzo[1,3]dioxole-5-carboxylic acid [19.88 g (73%)].

Workup

  1. temperatureheated to 100° C. for 1 hour
  2. filtrationThe reaction mixture was filtered through Celite®, acetone
  3. customwas removed in vacuo
  4. customthe product precipitated from the water solution by acidification to pH 1.2 with concentrated hydrochloric acid

Sources & evidence

ORD record
ord-9415a59e813648f4bdd520f926a15a3e
Source dataset
uspto-grants-2002_01
Patent number
US06335344B1

Reaction notes

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