Diethyl Ether → 3-Methyl-3-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-2-propenoic acid

HRID 4744Notes

Reaction equation

HRID 4744 reaction equation
BrC(C)C([C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:23])([C:19]([F:22])([F:21])[F:20])[C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)C(OC)=O.CC[O:27]CC.[O:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>>[CH3:31][C:32]([C:8]1[CH:9]=[CH:10][C:11]([C:14]([OH:23])([C:15]([F:16])([F:18])[F:17])[C:19]([F:21])([F:22])[F:20])=[CH:12][CH:13]=1)=[CH:33][C:34]([OH:30])=[O:27]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 20151848Methyl 3-bromo-3-methyl-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}propanoate

Product 1

HCID 541037613-Methyl-3-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-2-propenoic acid

Procedure

To a solution of methyl 3-bromo-3-methyl-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}propanoate in tetrahydrofuran can be added an equivalent amount of 1,5-diazabicyclo[3.4.0]nonene-5. The resulting reaction mixture can be stirred at elevated temperature until thin layer chromatographic analysis of a reaction sample indicates the reaction to be complete. The solvent can be removed and the residual oil dissolved in ether to obtain an ether solution which can be extracted with 1N hydrochloride acid and then by 2N sodium hydroxide solution. The resulting sodium hydroxide solution can be heated on the steam bath, cooled and made acidic with concentrated hydrochloric acid to obtain a product which can be isolated from the aqueous phase with ether. The resulting ether solution can be dried with anhydrous magnesium sulfate, filtered, and evaporated to give 3-methyl-3-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-2-propenoic acid.

Workup

  1. customThe resulting reaction mixture
  2. customthe reaction
  3. customThe solvent can be removed
  4. dissolutionthe residual oil dissolved in ether
  5. customto obtain an ether solution which
  6. extractioncan be extracted with 1N hydrochloride acid
  7. temperatureThe resulting sodium hydroxide solution can be heated on the steam bath
  8. temperaturecooled
  9. customto obtain a product which
  10. dry with materialThe resulting ether solution can be dried with anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-d619ebd614624d4388075e24b6d34182
Source dataset
uspto-grants-1988_02
Patent number
US04727180

Reaction notes

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