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

HRID 1903265Notes

Reaction equation

HRID 1903265 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.S(=O)(=O)(O)O.[N+:21]([O-])([OH:23])=[O:22]>>[N+:21]([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-:23])=[O:22]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 127197761-Phenylcyclopropane-1,2-dicarboxylic acid

Product 1

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

Procedure

To a stirred slurry of 20.6 g. of 1-phenylcyclopropane-1,2-dicarboxylic acid (J. Med. Chem. 24:481) 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 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.

Workup

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

Sources & evidence

ORD record
ord-8b6cb1b9f27449c4a3168dd1349f524d
Source dataset
uspto-grants-1984_03
Patent number
US04435419

Reaction notes

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