Hydrochloric Acid → 2-[(4-Fluorophenyl)methylidene]cyclohexan-1-one

HRID 271834Notes

Reaction equation

HRID 271834 reaction equation
[OH-].[K+].[F:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.[C:12]1(=[O:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.Cl>CCOC(C)=O>[F:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[C:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:12]2=[O:18])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7967CyclohexanoneHCID 14797Potassium HydroxideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 542282142-[(4-Fluorophenyl)methylidene]cyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

An aqueous KOH (0.25 g in 4.4 mL water) solution was added to p-fluorobenzaldehyde Compound 10a (1.04 mL, 10 mMol) and the mixture was heated to 65° C. Cyclohexanone Compound 2a (1.03 mL, 10 mMol) was added dropwise over 10 min and the reaction mixture was refluxed for 5 hrs, then cooled to r.t. and stirred at r.t. overnight. The reaction mixture was acidified with 1N HCl (26 mL) and diluted with EtOAc. The organic layer was separated and washed with brine, then dried with anhydrous sodium sulfate and filtered. The solvent was evaporated to provide a crude product which was then purified by silica gel column (eluted with 6% EtOAc in hexane) to give 2-(4-fluoro-benzylidene)-cyclohexanone Compound 10b (1.1 g, 54%).

Workup

  1. temperaturethe reaction mixture was refluxed for 5 hrs
  2. temperaturecooled to r.t.
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated
  8. customto provide a crude product which
  9. customwas then purified by silica gel column (eluted with 6% EtOAc in hexane)

Sources & evidence

ORD record
ord-6ab1f404a44a49be9e45e0b1f6d2a9b4
Source dataset
uspto-grants-2008_11
Patent number
US07452997B2

Reaction notes

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