Hydrochloric Acid → HCID 11436203, compound

HRID 421561Notes

Reaction equation

HRID 421561 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:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.Cl>O>[F:3][C:4]1[CH:11]=[CH:10][C:7](/[CH:8]=[C:13]2/[C:12](=[O:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]/2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10403CyclooctanoneHCID 14797Potassium HydroxideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 11436203HCID 11436203, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A solution of KOH (0.25 g, 4.46 mMol) in water (4.4 mL), was added to 4-fluoro-benzaldehyde Compound 2a (1.07 mL, 10 mMol) and the mixture was heated to 65° C. Cyclooctanone Compound 1a (1.26 g, 10 mMol) was added dropwise over a period of 15 mins. The mixture was refluxed for 5 hrs, then allowed to stir overnight at room temperature. The reaction mixture was acidified with 1N HCl (26 mL) and extracted with EtOAc (100 mL). The organic layer was washed with brine, dried over Na2SO4, then filtered and concentrated. The resulting yellow residue was purified on silica gel column with 3% EtOAc/Hexane to give (2E)-2-(4-fluoro-benzylidene)-cyclooctanone Compound 2b (1.04 g, 44.8%).

Workup

  1. temperatureThe mixture was refluxed for 5 hrs
  2. extractionextracted with EtOAc (100 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting yellow residue was purified on silica gel column with 3% EtOAc/Hexane

Sources & evidence

ORD record
ord-220e5fb84fc247eda0fe982f500709fd
Source dataset
uspto-grants-2012_01
Patent number
US08101592B2

Reaction notes

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