Sodium Hydroxide → (4,4-Difluorocyclohexyl)methanol

HRID 1443601Notes

Reaction equation

HRID 1443601 reaction equation
[F:1][C:2]1([F:13])[CH2:7][CH2:6][CH:5]([C:8](OCC)=[O:9])[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[F:1][C:2]1([F:13])[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2779138Ethyl-4,4-difluorocyclohexane carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 21184133(4,4-Difluorocyclohexyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under nitrogen atmosphere, 2.3 g of ethyl 4,4-difluorocyclohexanecarboxylate was dissolved in 50 ml of tetrahydrofuran. Thereto 0.46 g of lithium aluminum hydride was added at 0° C. and the mixture was stirred at 0° C. for an hour. Thereafter, 1N aqueous sodium hydroxide was added to the reaction mixture, and formed solids were filtered and then washed with ethyl acetate. The filtrate and the washing solution were combined, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain (4,4-difluorocyclohexyl)methanol.

Workup

  1. customformed solids
  2. filtrationwere filtered
  3. washwashed with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e3963d960814c74bfeb556bc3dd3677
Source dataset
uspto-grants-2010_02
Patent number
US07662402B2

Reaction notes

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