Sodium Hydroxide → (4,4-Difluorocyclohexyl)methanol

HRID 1520681Notes

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

Conditions

Temperature: 0 °C

Procedure

Lithium aluminum hydride (0.24 g) was slurried in diethyl ether (15 mL), ethyl 4,4-difluorocyclohexanecarboxylate (1.0 g) in diethyl ether (2 mL) was added dropwise, and the reaction was stirred under 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). Na2SO4 and diethyl ether (40 mL) were added and the mixture was stirred at room temperature for 30 minutes. Filtration through diatomaceous earth and concentration of the filtrate provided the title compound which was used without purification.

Workup

temperatureunder reflux under nitrogen for 4 hours
stirringthe mixture was stirred at room temperature for 30 minutes
filtrationFiltration through diatomaceous earth and concentration of the filtrate

Sources & evidence

ORD record: ord-334d2874117a4b7f96945c14beb7ac61
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073855B2

Reaction notes

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