Ethanol → 2-(4-Chlorobenzyloxy)-3,3,3-trifluoro-2-trifluoromethylpropionamide

HRID 2419893Notes

Reaction equation

HRID 2419893 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][C:8]([C:15]([F:18])([F:17])[F:16])([C:11]([F:14])([F:13])[F:12])[C:9]#[N:10])=[CH:4][CH:3]=1.[OH-].[K+].C([OH:25])C>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]([C:11]([F:12])([F:13])[F:14])([C:15]([F:16])([F:17])[F:18])[C:9]([NH2:10])=[O:25])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 133842982-(4-Chlorobenzyloxy)-3,3,3-trifluoro-2-trifluoromethylpropionitrile

Product 1

HCID 133842992-(4-Chlorobenzyloxy)-3,3,3-trifluoro-2-trifluoromethylpropionamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(4-chlorobenzyloxy)-3,3,3-trifluoro-2-trifluoromethylpropionitrile (20 g.), potassium hydroxide (25 g.), ethanol (250 ml.) and water (250 ml.) is heated under reflux for 15 minutes. Most of the ethanol is evaporated in vacuo, and the residue is cooled until the precipitated oil solidifies. The solid is filtered off, and is recrystallised from a mixture of ether and light petroleum (b.p. 40°-60° C.) (charcoal) to give 2-(4-chlorobenzyloxy)-3,3,3-trifluoro-2-trifluoromethylpropionamide, m.p. 94°-95° C. (13.9 g.).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 15 minutes
  3. customMost of the ethanol is evaporated in vacuo
  4. temperaturethe residue is cooled until the precipitated oil
  5. filtrationThe solid is filtered off
  6. customis recrystallised from a mixture of ether and light petroleum (b.p. 40°-60° C.) (charcoal)

Sources & evidence

ORD record
ord-cd33c756f5a4412e87f2c93fb50451fe
Source dataset
uspto-grants-1978_08
Patent number
US04107329

Reaction notes

Loading…