Sodium Hydroxide → (4,4-Difluorocyclohexyl)methanol

HRID 1043211Notes

Reaction equation

HRID 1043211 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+].[O-]S([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

Lithium aluminum hydride (0.24 g) was added to diethyl ether (15 mL), to which was then added dropwise ethyl 4,4-difluorocyclohexanecarboxylate (1.0 g) in diethyl ether (2 mL), and the reaction was stirred 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 additional water (0.72 mL). Then Na2SO4 and diethyl ether (40 mL) were added and the mixture was stirred for 30 minutes. After filtration through diatomaceous earth and concentration, the title compound was used in the next step without further purification.

Workup

  1. temperatureat reflux under nitrogen for 4 hours
  2. stirringthe mixture was stirred for 30 minutes
  3. filtrationAfter filtration
  4. concentrationthrough diatomaceous earth and concentration
  5. customthe title compound was used in the next step without further purification

Sources & evidence

ORD record
ord-b39dc07d3360453986cff86793bb7b63
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

Loading…