Tetrafluoroethylene → Ethyl 1-(4-ethoxyphenyl)-2,2,3,3-tetrafluorocyclobutane carboxylate

HRID 223466

Reaction equation

HRID 223466 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH3:15])=[CH:9][CH:8]=1)=[CH2:6])[CH3:2].[F:17][C:18]([F:22])=[C:19]([F:21])[F:20]>CC1C2C(C)(C)C(C2)CC=1.C1C=CC=CC=1>[CH2:14]([O:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2([C:4]([O:3][CH2:1][CH3:2])=[O:16])[CH2:6][C:18]([F:22])([F:17])[C:19]2([F:21])[F:20])=[CH:8][CH:9]=1)[CH3:15]

Participants

5

Reactant 2

HCID 8301TetrafluoroethyleneHCID 6454764Benzeneacetic acid, 4-ethoxy-alpha-methylene-, ethyl ester

Product 1

HCID 13239546Ethyl 1-(4-ethoxyphenyl)-2,2,3,3-tetrafluorocyclobutane carboxylateYield 75%

Reagents, catalysts & solvents 2

HCID 6654(+-)-alpha-PineneCatalystHCID 241BenzeneSolvent

Procedure

2-(4-ethoxyphenyl)propenoic acid ethyl ester (13.2 g) was mixed with benzene (7.5 ml), α-pinene (2 drops) N-ethyldiisopropyl amine (2 drops) and tetrafluoroethylene (15.5 ml) and heated to 150°-155° for 24 hours then 155°-60° C. for 17 hours. After evaporation of volatile materials the residue (16.6 g) was dissolved in dichloromethane and chromatographed on a column of silica gel to give the ester as a colourless oil 14.5 g (75%). Analysis: C: 56.47%, H: 5.24%, F: 23.4%. C15H16F4O3 requires C: 56.25%, H: 5.04%, F: 23.7%.

Workup

  1. temperatureheated to 150°-155° for 24 hours
  2. customAfter evaporation of volatile materials the residue (16.6 g)
  3. dissolutionwas dissolved in dichloromethane
  4. customchromatographed on a column of silica gel

Sources & evidence

ORD record
ord-59876c69c29948efa68791aff5a37767
Source dataset
uspto-grants-1982_10
Patent number
US04355042

Linked notes

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