Sodium Hydroxide → HCID 22261446, compound

HRID 1610530Notes

Reaction equation

HRID 1610530 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:18]=[CH:17][C:11]([C:12](OCC)=[O:13])=[CH:10][C:9]=1[O:19][C:20]([F:25])([F:24])[CH:21]([F:23])[F:22].[OH-].[Na+]>O1CCCC1>[CH3:7][C:8]1[CH:18]=[CH:17][C:11]([CH2:12][OH:13])=[CH:10][C:9]=1[O:19][C:20]([F:24])([F:25])[CH:21]([F:23])[F:22]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22262273HCID 22262273, compound

Product 1

HCID 22261446HCID 22261446, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminum hydride (1.02 g, 26.8 mmol) in tetrahydrofuran (100 ml) was added a solution of ethyl 4-methyl-3-((1,1,2,2-tetrafluoroethyl)oxy)benzoate (5.0 g, 17.8 mmol) in tetrahydrofuran (20 ml) under ice-cooling. After the reaction solution was stirred at room temperature for 30 min., 1N aqueous sodium hydroxide solution (20 ml) was added, and the mixture was filtered with celite. The filtrate was concentrated and water was added. The mixture was extracted with ethyl acetate (50 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to give (4-methyl-3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)methanol (4.45 g, 100%) as a colorless oil.

Workup

  1. temperaturecooling
  2. filtrationthe mixture was filtered with celite
  3. concentrationThe filtrate was concentrated
  4. additionwater was added
  5. extractionThe mixture was extracted with ethyl acetate (50 ml×2)
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-05a85a88c4e641139ee2ac2fa7c503b9
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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