Nitric Acid → 1-Methyl-2-nitro-3-(trifluoromethyl)benzene
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.C1(C(F)(F)F)C=CC=CC=1>C(Cl)Cl>[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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -18 °C
Procedure
The nitration vessel is charged with 250 gms (3.97 moles) of 98% HNO3 and cooled to about -18° C. Then 100 gms (0.62 moles) of 3-methyl benzotrifluoride is added dropwise with stirring and the temperature is maintained within the range of about -16° C. to about -22° C. The addition of the benzotrifluoride takes about 2 hours and 15 minutes. After it has been added, stirring is continued for about another 15 minutes. The reaction mixture is poured into ice water and methylene chloride is added to phase separate the nitration products. The organic layer is washed with sodium carbonate solution. The solvent is then stripped on a rotary evaporator. Yield is 127.5 gms of oil comprising 43% 2-nitro isomer; 31% 4-nitro isomer, 24% 6-nitro isomer and about 1% of the 5-nitro isomer as determined by glc and 19F NMR.
Workup
- temperaturethe temperature is maintained within the range of about -16° C. to about -22° C
- additionAfter it has been added
- stirringstirring
- customis continued for about another 15 minutes
- additionis added to phase
- customseparate the nitration products
- washThe organic layer is washed with sodium carbonate solution
- customThe solvent is then stripped on a rotary evaporator
Sources & evidence
- ORD record
- ord-fa67449060fa4d18a433c2884a761326
- Source dataset
- uspto-grants-1984_08
- Patent number
- US04467125
Reaction notes
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