Sodium Hydroxide → (4,4-Difluorocyclohexyl)methanol

HRID 2045086Notes

Reaction equation

HRID 2045086 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1([F:19])[CH2:13][CH2:12][CH:11]([C:14](OCC)=[O:15])[CH2:10][CH2:9]1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)C.O>[F:7][C:8]1([F:19])[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]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

To a slurry of lithium aluminum hydride (0.24 g) in diethyl ether (15 mL) was added dropwise ethyl 4,4-difluorocyclohexanecarboxylate (1.0 g) in diethyl ether (2 mL). The reaction heated at reflux under nitrogen for 4 hours. The reaction was cooled to 0° C., followed by the careful addition of water (0.24 mL), 4N aqueous NaOH (0.24 mL), and water (0.72 mL). The reaction was diluted with diethyl ether (40 mL) and stirred with sodium sulfate for 30 minutes. The mixture was filtered though diatomaceous earth and the filtrate was concentrated to provide the title compound.

Workup

  1. temperatureThe reaction heated
  2. temperatureat reflux under nitrogen for 4 hours
  3. filtrationThe mixture was filtered though diatomaceous earth
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ef3c79aab8c54e17a94416c2b51a4f8d
Source dataset
uspto-grants-2013_11
Patent number
US08586754B2

Reaction notes

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