Nitric Acid → 1-(4-Nitrophenyl)cyclopropanecarboxylic acid

HRID 1375091Notes

Reaction equation

HRID 1375091 reaction equation
[N+:1]([O-:4])([OH:3])=[O:2].[C:5]1([C:11]2([C:14]([OH:16])=[O:15])[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>>[N+:1]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:11]1([C:14]([OH:16])=[O:15])[CH2:13][CH2:12]1)([O-:4])=[O:2].[N+:1]([C:8]1[CH:9]=[CH:10][C:5]([C:11]2([C:14]([OH:16])=[O:15])[CH2:13][CH2:12]2)=[CH:6][CH:7]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 802061-Phenylcyclopropanecarboxylic acid

Product 2

HCID 200261851-(4-Nitrophenyl)cyclopropanecarboxylic acidHCID 210779211-(2-Nitrophenyl)cyclopropane-1-carboxylic acid

Conditions

Temperature
0 °C

Procedure

A stirred solution of fuming nitric acid (1.6 mL), at −30° C. and under nitrogen, was treated portionwise with 1-phenyl-cyclopropanecarboxylic acid (10 g). The reaction mixture was allowed to warm to 0° C., then stirred at this temperature for 2 hours and then poured into ice(100 g). The resulting solid was filtered, then washed well with water, then dried at 60° C. under vacuo and then recrystallised from toluene to give 1-(2-nitro-phenyl)-cyclopropanecarboxylic acid and 1-(4-nitro-phenyl)-cyclopropanecarboxylic acid (11.35 g). MS(ES−): 206 (M−H)−.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed well with water
  3. customdried at 60° C. under vacuo
  4. customrecrystallised from toluene

Sources & evidence

ORD record
ord-2e6a4647ef2c48a88e8547df776f121b
Source dataset
uspto-grants-2007_01
Patent number
US07166616B2

Reaction notes

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