Methanol → 4,4,4-Trifluoro-2,2-dimethylbutan-1-ol

HRID 1616246Notes

Reaction equation

HRID 1616246 reaction equation
[F:1][C:2]([F:13])([F:12])[CH2:3][C:4]([CH3:11])([CH3:10])[C:5](OCC)=[O:6].[H-].[H-].[H-].[H-].[Li+].[Al+3].CO>CCOCC>[F:1][C:2]([F:13])([F:12])[CH2:3][C:4]([CH3:11])([CH3:10])[CH2:5][OH:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 9990309Ethyl 2,2-dimethyl-4,4,4-trifluorobutanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 597069974,4,4-Trifluoro-2,2-dimethylbutan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of ethyl 4,4,4-trifluoro-2,2-dimethylbutanoate (1 g, 5.05 mmol) in ether (25 ml) under nitrogen was added LAH (1M solution in ether, 20.2 mmol) and allowed to stir at room temperature for one hour. Methanol was slowly added to R×n until bubbling stopped. The reaction was then suspended in ether and Water. The suspension was washed with Water, dried over sodium sulfate, filtered, and concentrated without heat to produce an oil 4,4,4-trifluoro-2,2-dimethylbutan-1-ol (75-1). 1H NMR (500 MHz, CDCl3) δ 3.4 (s, 2H), 2.20-2.01 (m, 2H), 1.05 (s, 6H). (M+H)+: observed=157.16, calculated=157.15

Workup

  1. customuntil bubbling
  2. washThe suspension was washed with Water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. temperaturewithout heat

Sources & evidence

ORD record
ord-acc82fe7a09441d99dc41e8240c65117
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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