Ethyl-4,4-difluorocyclohexane carboxylate → (4,4-Difluorocyclohexyl)methanol

HRID 78542

Reaction equation

HRID 78542 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>C(OCC)C>[F:7][C:8]1([F:19])[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1

Participants

4

Reactant 2

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

Product 1

HCID 21184133(4,4-Difluorocyclohexyl)methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminum hydride (2.6 g, 69 mmol) in diethyl ether (160 mL) was added slowly a solution of commercially available ethyl 4,4-difluorocyclohexanecarboxylate (Matrix, 11.0 g, 57 mmol) in diethyl ether (20 mL). The reaction mixture was refluxed for 4 hours, then cooled in an ice bath, quenched cautiously with sequential addition of water (2.6 mL), 15% NaOH (2.6 mL) and water (7.8 mL) and extracted with ethyl acetate (3×100 mL). The mixture was filtered and concentrated to afford the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. temperaturecooled in an ice bath
  3. customquenched cautiously with sequential addition of water (2.6 mL), 15% NaOH (2.6 mL) and water (7.8 mL)
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b37d234b369c4db8b1e9ef646315aa1b
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

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