Water → 3-(Trifluoromethyl)-4-isopropoxynitrobenzene

HRID 1862790Notes

Reaction equation

HRID 1862790 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:7][C:8]=1Cl.[CH3:15][CH:16]([CH3:18])[O-:17].[Na+].O>CS(C)=O>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:7][C:8]=1[O:17][CH:16]([CH3:18])[CH3:15]

Participants

5

Reactant 3

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

Product 1

HCID 105385593-(Trifluoromethyl)-4-isopropoxynitrobenzeneYield 92.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a chilled (5° C.) solution of 118 g (0.5 mole) of 3-(trifluoromethyl)-4-chloronitrobenzene in 100 ml of dimethyl sulfoxide (DMSO) was added dropwise a solution containing 41 g (0.5 mole) of sodium isopropoxide in 300 ml of dimethyl sulfoxide. The dark reaction mixture was stirred at ambient temperature for one hour, poured into water and extracted with ether. The ether extracts were washed with water, dried and concentrated. Recrystallization of the residual liquid from hexane gave 115.5 g (92.7%) of white crystalline solid; m.p. 34°-36°.

Workup

  1. additionwas added dropwise a solution
  2. customThe dark reaction mixture
  3. extractionextracted with ether
  4. washThe ether extracts were washed with water
  5. customdried
  6. concentrationconcentrated
  7. customRecrystallization of the residual liquid from hexane

Sources & evidence

ORD record
ord-e89af119b6cd42bdaf77c49abeca2436
Source dataset
uspto-grants-1979_09
Patent number
US04166735

Reaction notes

Loading…