Ethyl Acrylate → 4-(5,5,6,6,7,7,8,8,8-Nonafluoro-octyl)-cyclohex-3-enecarboxylic Acid Ethyl Ester

HRID 48111

Reaction equation

HRID 48111 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]([F:25])([C:15]([F:24])([F:23])[C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([CH:13]=[CH2:14])=[CH2:12].[C:26]([O:30][CH2:31][CH3:32])(=[O:29])[CH:27]=[CH2:28]>C1(C)C=CC=CC=1>[CH2:31]([O:30][C:26]([CH:27]1[CH2:28][CH2:12][C:11]([CH2:10][CH2:9][CH2:8][CH2:7][C:6]([F:25])([F:5])[C:15]([F:23])([F:24])[C:16]([F:21])([F:22])[C:17]([F:18])([F:19])[F:20])=[CH:13][CH2:14]1)=[O:29])[CH3:32]

Participants

5

Reactant 3

HCID 8821Ethyl AcrylateHCID 6451240Aluminum(III) ChlorideHCID 206321542-(5,5,6,6,7,7,8,8,8-Nonafluoro-octyl)-buta-1,3-diene

Product 1

HCID 867593684-(5,5,6,6,7,7,8,8,8-Nonafluoro-octyl)-cyclohex-3-enecarboxylic Acid Ethyl EsterYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a slurry of aluminum chloride (0.1 equi) in toluene (1 mL/mmole), ethyl acrylate (1 equi.) (1 equi.) was added at ice temperature. The reaction mixture was stirred at ice temperature for 10 min. Then a solution 2-(5,5,6,6,7,7,8,8,8-nonafluoro-octyl)-buta-1,3-diene (40) (0.5M in THF) (1 equi.) was added at ice temperature over a period of 20 min. The reaction mixture was stirred at ice temperature for 10 h, water, extracted with hexane, washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (hexanes) gave 4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyl)-cyclohex-3-enecarboxylic acid ethyl ester (41) as a colorless oil (88%).

Workup

  1. stirringThe reaction mixture was stirred at ice temperature for 10 h
  2. extractionwater, extracted with hexane
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography on silica gel (hexanes)

Sources & evidence

ORD record
ord-487cb1cdebea42d59d94f98259f552fc
Source dataset
uspto-grants-2004_03
Patent number
US06703082B1

Linked notes

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