Hydrogen Peroxide → 5,5,5-Trifluoro-3-methyl-2-(4-methylphenyl)pentan-1-ol

HRID 877199Notes

Reaction equation

HRID 877199 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]([CH3:16])[CH2:11][C:12]([F:15])([F:14])[F:13])=[CH2:9])=[CH:4][CH:3]=1.[OH-:17].[Na+].OO.[Cl-].[Na+]>C1COCC1.O>[F:15][C:12]([F:14])([F:13])[CH2:11][CH:10]([CH3:16])[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)[CH2:9][OH:17]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 581364211-Methyl-4-(5,5,5-trifluoro-3-methylpent-1-en-2-yl)benzene

Product 1

HCID 581366425,5,5-Trifluoro-3-methyl-2-(4-methylphenyl)pentan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under argon, 9.4 g (41.2 mmol) of 1-methyl-4-(5,5,5-trifluoro-3-methylpent-1-en-2-yl)benzene were dissolved in 130 ml of THF, 57.6 ml of a 1 M borane/THF complex solution were added and the mixture was stirred at room temperature for 24 h. With vigorous stirring, initially 79 ml of water, then 24 ml of 6 M aqueous sodium hydroxide solution and finally 14.5 ml (475 mmol) of 30% strength aqueous hydrogen peroxide solution were added. Subsequently, the reaction solution was added to 200 ml of saturated sodium chloride solution, the organic phase was separated off and the aqueous phase was extracted three more times with diethyl ether. The combined organic phases were dried over magnesium sulfate and filtered, and the solvent was removed under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 4:1→2:1). This gave 5 g (20.3 mmol, 49% of theory) of the title compound as a colorless oil.

Workup

  1. addition57.6 ml of a 1 M borane/THF complex solution were added
  2. customthe organic phase was separated off
  3. extractionthe aqueous phase was extracted three more times with diethyl ether
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 4:1→2:1)

Sources & evidence

ORD record
ord-ab118547e212479f81f202c2e94239cd
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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