Nitric Acid → 1-Methyl-2-nitro-3-(trifluoromethyl)benzene

HRID 358417Notes

Reaction equation

HRID 358417 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[CH:7]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:10][CH:11]=1>>[N+:1]([C:7]1[C:6]([CH3:5])=[CH:11][CH:10]=[CH:9][C:8]=1[C:12]([F:13])([F:15])[F:14])([O-:4])=[O:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 1362463-Methylbenzotrifluoride

Product 1

HCID 134554311-Methyl-2-nitro-3-(trifluoromethyl)benzene

Conditions

Temperature
10 °C

Procedure

6 gms of 90% nitric acid is cooled to -5° C. and 2 gms of 3-methyl benzotrifluoride was added dropwise with stirring. The two phase system was allowed to warm to 10° C. during addition. After stirring 2 hours, the reaction mixture was poured onto ice, extracted with methylene chloride and washed with dilute aqueous sodium bicarbonate. After vacuum removal of solvent on a rotary evaporator, near quantitative oil was obtained which had isomer distribution:

Workup

  1. stirringAfter stirring 2 hours
  2. additionthe reaction mixture was poured onto ice
  3. extractionextracted with methylene chloride
  4. washwashed with dilute aqueous sodium bicarbonate
  5. customAfter vacuum removal of solvent
  6. customon a rotary evaporator
  7. customnear quantitative oil was obtained which

Sources & evidence

ORD record
ord-be14b42b0cec471ea2c5bcb72778e868
Source dataset
uspto-grants-1984_08
Patent number
US04467125

Reaction notes

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