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

HRID 973292Notes

Reaction equation

HRID 973292 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-fe8f915bc1f54480986a27178c9246ce
Source dataset
uspto-grants-1977_10
Patent number
US04055595

Reaction notes

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