Sodium Hydroxide → (4,4-Difluorocyclohexyl)methanol

HRID 2168079Notes

Reaction equation

HRID 2168079 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+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C(OCC)C.O>[F:1][C:2]1([F:13])[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 2779138Ethyl-4,4-difluorocyclohexane carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 21184133(4,4-Difluorocyclohexyl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

Ethyl 4,4-difluorocyclohexanecarboxylate (1.0 g, 5.20 mmol) in diethyl ether (2 mL) was added dropwise to lithium aluminium hydride (0.24 g) in diethyl ether (15 mL), and heated under reflux for 4 hours. The reaction was then cooled to 0° C., and water was added (0.24 mL), followed by 5N aqueous NaOH (0.24 mL) and water (0.72 mL). Then Na2SO4 and more diethyl ether (40 mL) were added, and the mixture was stirred for 30 minutes, then filtered through celite. After concentration, the residue was diluted with CH2Cl2 and Na2SO4 was added, and the mixture was filtered and concentrated to provide the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. filtrationfiltered through celite
  4. concentrationAfter concentration
  5. additionthe residue was diluted with CH2Cl2 and Na2SO4
  6. additionwas added
  7. filtrationthe mixture was filtered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b423b2395d8a44e5820fbe1c19f3d72c
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

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