1,1,1,3,3-Pentafluoro-2,3-dichloro-2-(4-ethoxyphenyl)propane → 1,1,1,3,3-Pentafluoro-2-(4-ethoxyphenyl)prop-2-ene

HRID 483729Notes

Reaction equation

HRID 483729 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3](Cl)([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][CH:9]=1)[C:4]([F:7])([F:6])Cl>CO.[Zn].[Cl-].[Zn+2].[Cl-]>[F:1][C:2]([F:18])([F:19])[C:3]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][CH:9]=1)=[C:4]([F:6])[F:7]

Participants

5

Reactant 1

HCID 145170441,1,1,3,3-Pentafluoro-2,3-dichloro-2-(4-ethoxyphenyl)propane

Product 1

HCID 145170451,1,1,3,3-Pentafluoro-2-(4-ethoxyphenyl)prop-2-eneYield 82.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×

Conditions

Temperature
35 °C

Procedure

A solution of 1,1,1,3,3-pentafluoro-2, 3-dichloro-2-(4-ethoxyphenyl)propane (29.5 g) in methanol (40 cm3) was added dropwise to a suspension of zinc powder (9.1 g) and zinc chloride (0.45 g) in methanol (80 cm3) whilst the temperature was maintained at 35° C. After the addition was complete the mixture was stirred at the ambient temperature ca. 23° C.) for 2 hours. After dilution with water and filtering off the zinc, the mixture was extracted with chloroform, the extracts washed with water, dried over anhydrous magnesium sulphate and concentrated by evaporation of the solvent to yield 1,1,1,3,3-pentafluoro-2-(4-ethoxyphenyl)prop-2-ene (19.0 g) as a mobile liquid.

Workup

  1. additionAfter the addition
  2. filtrationAfter dilution with water and filtering off the zinc
  3. extractionthe mixture was extracted with chloroform
  4. washthe extracts washed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. concentrationconcentrated by evaporation of the solvent

Sources & evidence

ORD record
ord-729c8283537b436bbb5e3a310675284c
Source dataset
uspto-grants-1993_07
Patent number
US05225607

Reaction notes

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