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

HRID 365024Notes

Reaction equation

HRID 365024 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].Cl[C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1.[OH-].[K+]>COCCOCCOCCOCCOC>[F:13][C:12]([F:15])([F:14])[C:9]1[CH:10]=[CH:11][C:6]([O:4][CH:1]=[CH:2][CH3:3])=[CH:7][CH:8]=1

Participants

5

Reactant 3

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

Product 1

HCID 86740963Propenyl 4-trifluoromethylphenyl etherYield 67.7%

Reagents, catalysts & solvents 1

HCID 8925TetraglymeCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of 4.0 kg of allyl alcohol and 6.2 kg of 4-chlorobenzotrifluoride was added over 6 hours to a stirred mixture of 6.8 kg of 85% potassium hydroxide and 17.4 g of tetraglyme at 80° C. The temperature was then raised to 100° C. for 2.5 hours, after which time the reaction mixture was cooled and distilled, and the residue was triturated with toluene and re-distilled to give 4.7 kg of propenyl 4-trifluoromethylphenyl ether.

Workup

  1. temperatureafter which time the reaction mixture was cooled
  2. distillationdistilled
  3. customthe residue was triturated with toluene
  4. distillationre-distilled

Sources & evidence

ORD record
ord-6ed8b21f5b884b96988dd8d3b4739912
Source dataset
uspto-grants-1986_08
Patent number
US04607128

Reaction notes

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