Cyclohexanol → HCID 11962050, compound

HRID 222858Notes

Reaction equation

HRID 222858 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].F[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1>CN(C)C=O>[CH:1]1([O:7][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7966CyclohexanolHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydride

Product 1

HCID 11962050HCID 11962050, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 3.9 g of cyclohexanol (1.1 equivalents) put into the presence of 2.12 g of sodium hydride (1.5 equivalents) under stirring for 10 min, is added a solution of 5 g of 4-fluoronitrobenzene in 75 mL of dimethylformamide. The whole is heated to 60° C. for 5 hrs. After returning to room temperature, the medium is hydrolyzed and the reaction crude product is extracted with ethyl acetate several times. The organic phases are dried on magnesium sulfate, filtered and evaporated under reduced pressure. With a silica gel chromatography of the residue (cyclohexane and then cyclohexane/ethyl acetate: 98/2 and 90/10) 6.06 g of the desired product are able to be isolated.

Workup

  1. customAfter returning to room temperature
  2. customthe reaction crude product
  3. extractionis extracted with ethyl acetate several times
  4. customThe organic phases are dried on magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto be isolated

Sources & evidence

ORD record
ord-aab12bc5d989400caad636e918ce3c71
Source dataset
uspto-grants-2012_06
Patent number
US08207373B2

Reaction notes

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