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

HRID 1719571Notes

Reaction equation

HRID 1719571 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 aqeuous 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-acc151872dd64e9f867ab4b9ee21415a
Source dataset
uspto-grants-1985_09
Patent number
US04540710

Reaction notes

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