Dichloromethane → 3-(2,2,3,3,3-Pentafluoropropoxy)methyl-4-methyl-1-nitrobenzene

HRID 373361

Reaction equation

HRID 373361 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH2:4]Cl.[F:13][C:14]([F:21])([C:17]([F:20])([F:19])[F:18])[CH2:15][OH:16].[OH-].[K+].ClCCl>CN(C)C=O>[F:13][C:14]([F:21])([C:17]([F:20])([F:19])[F:18])[CH2:15][O:16][CH2:4][C:3]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 98722,2,3,3,3-PentafluoropropanolHCID 14797Potassium HydroxideHCID 1879522-(Chloromethyl)-1-methyl-4-nitrobenzene

Product 1

HCID 150701683-(2,2,3,3,3-Pentafluoropropoxy)methyl-4-methyl-1-nitrobenzeneYield 95.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.00 g (0.027 mol) of 2-methyl-5-nitrobenzyl chloride and 21.3 g (0.135 mol) of 2,2,3,3,3-pentafluoropropanol in 16.5 ml of dimethylformamide, was added 2.29 g (0.041 mol) of KOH pellets and the solution was stirred overnight. Then dichloromethane was added and the salts were filtered out. The filtrate was made acid and then the solvents were distilled off. The residue was dissolved in a 9/1 (v/v) mixed solvent of hexane/ethyl acetate, washed with dilute hydrochloric acid, water and a saturated sodium chloride aqueous solution, and then dried over magnesium sulfate. The solvents were distilled off and the resulting oil was subjected to silica gel chromatography using hexane/ethyl acetate (19/1, v/v) as developing solvent to obtain 7.71 g of 3-(2,2,3,3,3-pentafluoropropoxy)methyl-4-methyl-1-nitrobenzene having a melting point of 53.5°-54.5° C. in a 95.5% yield.

Workup

  1. filtrationthe salts were filtered out
  2. distillationthe solvents were distilled off
  3. dissolutionThe residue was dissolved in a 9/1 (v/v)
  4. additionmixed solvent of hexane/ethyl acetate
  5. washwashed with dilute hydrochloric acid, water
  6. dry with materiala saturated sodium chloride aqueous solution, and then dried over magnesium sulfate
  7. distillationThe solvents were distilled off

Sources & evidence

ORD record
ord-d18683146e0c4b8989faee8f8e73a498
Source dataset
uspto-grants-1992_11
Patent number
US05162583

Linked notes

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