Sulfuric Acid → 5-Ethoxycarbonyloxy-2-nitrobenzoic acid

HRID 371625Notes

Reaction equation

HRID 371625 reaction equation
[C:1](=[O:17])([O:14][CH2:15][CH3:16])[O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([CH:12]=[O:13])[CH:4]=1.[Mn]([O-])(=O)(=O)=[O:19].[K+].S(=O)(=O)(O)O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(Cl)(Cl)Cl.CC(C)=O.C(O)(=O)C>[C:1](=[O:17])([O:14][CH2:15][CH3:16])[O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([C:12]([OH:19])=[O:13])[CH:4]=1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 339208Ethyl (3-formyl-4-nitro-phenyl) carbonateHCID 516875Potassium PermanganateHCID 656671Sodium Pyrosulfite

Product 1

HCID 205022675-Ethoxycarbonyloxy-2-nitrobenzoic acidYield 84.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 6212ChloroformSolvent

Procedure

A stirred mixture of 3-formyl-4-nitrophenyl ethyl carbonate (33.1 g, prepared as described in J. Chem. Soc., 1925, 1195), potassium permanganate (17.0 g), acetic acid (33 ml) and acetone (330 ml) was cooled to keep the temperature below 50°, then allowed to stand at room temperature for a further 45 minutes. Dilute sulphuric acid and chloroform were added and the mixture decolorised with sodium metabisulphite. The organic layer was extracted with sodium bicarbonate solution and the extracts acidified with dilute hydrochloric acid to give 3-carboxy-4-nitrophenyl ethyl carbonate (23.2 g, m.p. 132°-7°).

Workup

  1. temperaturewas cooled
  2. customthe temperature below 50°
  3. extractionThe organic layer was extracted with sodium bicarbonate solution

Sources & evidence

ORD record
ord-f07c90637d164f7ab75eb5bc0dc2237c
Source dataset
uspto-grants-1978_05
Patent number
US04087422

Reaction notes

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