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

HRID 66289Notes

Reaction equation

HRID 66289 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 stirred 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 tmperature 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-b81aac3a5aaa417396941f5f30936e4c
Source dataset
uspto-grants-1978_12
Patent number
US04131611

Reaction notes

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