Hydrochloric Acid → 2-{3-[2,2,2-Trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}ethanol

HRID 4755Notes

Reaction equation

HRID 4755 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([C:9]1[CH:10]=[C:11]([CH2:15][C:16](O)=[O:17])[CH:12]=[CH:13][CH:14]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].Cl.[H][H]>O1CCCC1>[F:1][C:2]([F:19])([F:20])[C:3]([C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][OH:17])[CH:12]=[CH:13][CH:14]=1)([OH:8])[C:4]([F:5])([F:7])[F:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 201518553-[2,2,2-Trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzeneactic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 140766652-{3-[2,2,2-Trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}ethanolYield 38.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To one liter of 1M borane-tetrahydrofuran complex was added a solution of 100 g (0.33 mole) of 3-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzeneactic acid in 200 ml of tetrahydrofuran. The solution is refluxed for 16 hours under nitrogen. The solution is then refluxed with 400 ml of 6N hydrochloric acid until evolution of hydrogen is complete. The mixture is filtered and evaporated. The residue is refluxed with 500 ml of methanol containing 10 ml of concentrated hydrochloric acid until methyl borate is no longer evolved. The solution is evaporated, and the residue is distilled at 110°-115° (0.7 mm) to give 37 g of 2-{3-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}ethanol.

Workup

  1. temperatureThe solution is refluxed for 16 hours under nitrogen
  2. filtrationThe mixture is filtered
  3. customevaporated
  4. temperatureThe residue is refluxed with 500 ml of methanol containing 10 ml of concentrated hydrochloric acid until methyl borate
  5. customThe solution is evaporated
  6. distillationthe residue is distilled at 110°-115° (0.7 mm)

Sources & evidence

ORD record
ord-23f42f8623e741769a45a5605a83b535
Source dataset
uspto-grants-1988_02
Patent number
US04727180

Reaction notes

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