Nitric Acid → 1-(4-Nitrophenyl)-1,2-cyclopropanedicarboxylic acid

HRID 2048996Notes

Reaction equation

HRID 2048996 reaction equation
[C:1]1([C:7]2([C:13]([OH:15])=[O:14])[CH2:9][CH:8]2[C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:16]([O-])([OH:18])=[O:17]>S(=O)(=O)(O)O>[N+:16]([C:4]1[CH:3]=[CH:2][C:1]([C:7]2([C:13]([OH:15])=[O:14])[CH2:9][CH:8]2[C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 127197761-Phenylcyclopropane-1,2-dicarboxylic acid

Product 1

HCID 128913651-(4-Nitrophenyl)-1,2-cyclopropanedicarboxylic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a slurry of 20.6 g. of 1-phenylcyclopropane-1,2-dicarboxylic acid in 25 ml of concentrated sulfuric acid at 0° C. is added 15 ml of concentrated nitric acid over 30 minutes. The resultant solution is then stirred at ambient temperature for 30 minutes and then poured onto ice. The crystalline product is recrystallized from hexane-ethyl acetate to give 1-(p-nitrophenyl)-cyclopropane-1,2-dicarboxylic acid as colorless crystals, m.p. 138°-144° C.

Workup

  1. additionpoured onto ice
  2. customThe crystalline product is recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-70e63ad805404ee9b7d2814c2eaf56db
Source dataset
uspto-grants-1980_04
Patent number
US04196120

Reaction notes

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