Nitric Acid → 1-(4-Carboxy-2-nitrophenyl)-2-nitropropene

HRID 2412648Notes

Reaction equation

HRID 2412648 reaction equation
[N+:1]([O-])([OH:3])=[O:2].S(=O)(=O)(O)O.[C:10]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]=[C:20]([N+:22]([O-:24])=[O:23])[CH3:21])=[CH:15][CH:14]=1)([OH:12])=[O:11]>>[C:10]([C:13]1[CH:14]=[CH:15][C:16]([CH:19]=[C:20]([N+:22]([O-:24])=[O:23])[CH3:21])=[C:17]([N+:1]([O-:3])=[O:2])[CH:18]=1)([OH:12])=[O:11]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 542582771-(4-Carboxyphenyl)-2-nitropropene

Product 1

HCID 537891001-(4-Carboxy-2-nitrophenyl)-2-nitropropene

Procedure

Fuming nitric acid (95-98% w/w, 3.7 ml) was added dropwise with stirring to concentrated sulphuric acid (98% w/w, 30 ml), whilst maintaining the temperature at 0°-10° C. 1-(4-Carboxyphenyl)-2-nitropropene (15.3 g) was then added in portions with vigorous stirring over 15 minutes, whilst maintaining the temperature at 0°-10° C. The mixture was stirred for 30 minutes at the same temperature. The viscous reaction mixture was poured onto an ice/water mixture (600 ml) and the resulting yellow solid was filtered off and washed with water to give 1-(4-carboxy-2-nitrophenyl)-2-nitropropene (17.17 g), m.p. 200°-202° C. (with decomposition).

Workup

  1. temperaturewhilst maintaining the temperature at 0°-10° C
  2. temperaturewhilst maintaining the temperature at 0°-10° C
  3. stirringThe mixture was stirred for 30 minutes at the same temperature
  4. filtrationthe resulting yellow solid was filtered off
  5. washwashed with water

Sources & evidence

ORD record
ord-1acdf57792bf433781b4d5822ccec3c8
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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