Sodium Hydroxide → 1-(4-Ethoxyphenyl)-2,2,3,3-tetrafluorocyclobutane-1-carboxylic acid

HRID 223467Notes

Reaction equation

HRID 223467 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:18]([O:20]CC)=[O:19])[CH2:13][C:12]([F:15])([F:14])[C:11]2([F:17])[F:16])=[CH:6][CH:5]=1)[CH3:2].[OH-].[Na+]>C(O)C.O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:18]([OH:20])=[O:19])[CH2:13][C:12]([F:15])([F:14])[C:11]2([F:16])[F:17])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13239546Ethyl 1-(4-ethoxyphenyl)-2,2,3,3-tetrafluorocyclobutane carboxylate

Product 1

HCID 132395471-(4-Ethoxyphenyl)-2,2,3,3-tetrafluorocyclobutane-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 1-(4-ethoxyphenyl)-2,2,3,3-tetrafluorocyclobutane carboxylate (14.5 g) was dissolved in ethanol (100 ml) and a 10% w/w solution of sodium hydroxide in water (100 ml) was added and the mixture refluxed for 2.5 hours. The mixture was cooled, added to ice water and extracted with diethyl ether. The aqueous layer was acidified and the precipitate was filtered off, washed with water, dried and crystallised from 60°-80° petroleum ether to give the acid mp 112°-3° C. Yield 11.2 g (85%). Analysis: C: 53.20% H: 4.22%, F: 25.9%. C13H12F4O3 requires C: 53.43% H: 4.14% F: 26.0%.

Workup

  1. temperaturethe mixture refluxed for 2.5 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with diethyl ether
  4. filtrationthe precipitate was filtered off
  5. washwashed with water
  6. customdried
  7. customcrystallised from 60°-80° petroleum ether
  8. customto give the acid mp 112°-3° C

Sources & evidence

ORD record
ord-e91274c83ff34ba79f9d0c67ffc1daaf
Source dataset
uspto-grants-1982_10
Patent number
US04355042

Reaction notes

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