Acetic Acid → 2-Formyl-5-nitrobenzoic acid

HRID 1578765Notes

Reaction equation

HRID 1578765 reaction equation
[OH:1][CH2:2][C:3]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:4]=1[C:5](N(C)C)=[O:6].C(O)(=[O:19])C>O.[O-2].[O-2].[O-2].[Cr+6]>[C:5]([C:4]1[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:3]=1[CH:2]=[O:1])([OH:19])=[O:6]

Participants

5

Reactant 2

HCID 176Acetic Acid2×HCID 214230322-hydroxymethyl-5-nitro-N,N-dimethylbenzamide

Product 1

HCID 3436852-Formyl-5-nitrobenzoic acid

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent

Procedure

To a solution of 2-hydroxymethyl-5-nitro-N,N-dimethylbenzamide (17 g.) in glacial acetic acid (340 ml.) was added chromium trioxide (17 g.) in water (17 ml.) and glacial acetic acid (340-1). The reaction mixture was stirred at room temperature for 5 minutes, and then poured into ice-water (2 liters). The aqueous was extracted with chloroform (3 × 500 ml.). The chloroform extracts were combined and neutralised by washing with 10% sodium bicarbonate solution. The chloroform extracts were then washed thoroughly with water and dried over magnesium sulphate. The solution was then filtered and the solvent evaporated off to yield a gum.

Workup

  1. extractionThe aqueous was extracted with chloroform (3 × 500 ml.)
  2. washby washing with 10% sodium bicarbonate solution
  3. washThe chloroform extracts were then washed thoroughly with water
  4. dry with materialdried over magnesium sulphate
  5. filtrationThe solution was then filtered
  6. customthe solvent evaporated off
  7. customto yield a gum

Sources & evidence

ORD record
ord-7e04a3285ac84ef8915c27b962dd1481
Source dataset
uspto-grants-1976_02
Patent number
US03939180

Reaction notes

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