Water → 3-(Trifluoromethyl)-4-isopropoxynitrobenzene

HRID 127817Notes

Reaction equation

HRID 127817 reaction equation
[CH3:1][CH:2]([CH3:4])[O-:3].[Na+].Cl[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[C:16]([F:19])([F:18])[F:17].O>CS(C)=O>[CH:2]([O:3][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[C:16]([F:17])([F:18])[F:19])([CH3:4])[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 612132-Chloro-5-nitrobenzotrifluorideHCID 109204432-Propanol, sodium salt (1:1)

Product 1

HCID 105385593-(Trifluoromethyl)-4-isopropoxynitrobenzene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 41 g of sodium isopropoxide in 300 ml of dimethyl sulfoxide was added drop-by-drop to a chilled (5° C.) solution of 118 g of 2-chloro-5-nitrobenzotrifluoride in 100 ml of dimethyl sulfoxide. The resulting mixture was stirred at room temperature for one hour, poured into water, and the resulting mixture was extracted with ether. The extract was washed with water, dried, and the solvent was evaporated. The liquid residue was taken up in hexane and the solution was chilled to give a solid, which on recrystallization from hexane gave 2-isopropoxy-5-nitrobenzotrifluoride (2A), as a white crystalline solid, mp: 34°-36° C.

Workup

  1. extractionthe resulting mixture was extracted with ether
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was evaporated
  5. temperaturethe solution was chilled
  6. customto give a solid, which
  7. customon recrystallization from hexane

Sources & evidence

ORD record
ord-02ae50cfe1df482a904e6d0c58b914cb
Source dataset
uspto-grants-1981_03
Patent number
US04257805

Reaction notes

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