1-Chloro-4-(trifluoromethyl)benzene → Propenyl 4-trifluoromethylphenyl ether

HRID 365022

Reaction equation

HRID 365022 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].[OH-].[K+].Cl[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1>S1(CCCC1)(=O)=O>[F:15][C:14]([F:17])([F:16])[C:11]1[CH:12]=[CH:13][C:8]([O:4][CH:1]=[CH:2][CH3:3])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 73941-Chloro-4-(trifluoromethyl)benzeneHCID 7858Allyl AlcoholHCID 14797Potassium Hydroxide

Product 1

HCID 86740963Propenyl 4-trifluoromethylphenyl etherYield 68%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
30 °C

Procedure

174 g of allyl alcohol was added to a mixture of 298 g of 85% flake potassium hydroxide and 750 ml of sulpholane under nitrogen, and the mixture was heated to 125°-135° C. 272 g of 4-chlorobenzotrifluoride was added over 20 minutes at this temperature. After 2 hours, the reaction mixture was cooled to 30° C., and distillation from the solvent gave 207 g of propenyl 4-trifluoromethylphenyl ether b.p.: 84°-88° C. at 15 Torr.

Workup

  1. temperaturethe mixture was heated to 125°-135° C
  2. distillationdistillation from the solvent

Sources & evidence

ORD record
ord-be72b45bf65b4194a2433b74d140fc6c
Source dataset
uspto-grants-1986_08
Patent number
US04607128

Linked notes

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