2-Cyclohexen-1-OL → HCID 12039786, compound

HRID 1108749Notes

Reaction equation

HRID 1108749 reaction equation
I[C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH:10]1([OH:16])[CH2:15][CH2:14][CH2:13][CH:12]=[CH:11]1.C(=O)(O)[O-].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([CH:12]2[CH2:13][CH2:14][CH2:15][C:10](=[O:16])[CH2:11]2)[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 131982-Cyclohexen-1-OLHCID 69839Benzene, 1-iodo-3-methoxy-HCID 516893Potassium Bicarbonate

Product 1

HCID 12039786HCID 12039786, compoundYield 19.6%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

3-Iodoanisole (75g), 2-cyclohexen-1-ol (15g), potassium bicarbonate (45 g), tetrabutylammonium chloride (45 g) and palladium acetate (1.8 g) were heated and stirred for 80 hours at an external temperature of 60° C. and under an argon air flow, using acetonitrile (300 ml) as the solvent. After concentrating the reaction solution under reduced pressure, an aqueous ammonium chloride solution was added and extraction was performed with diethyl ether. After washing the organic layer with saturated saline, it was dried with anhydrous magnesium sulfate. The crude product obtained from distilling off the solvent under reduced pressure was separated and purified by silica gel chromatography (n-hexane:ethyl acetate=20:1) to give 6.1 g of 3-(3-methoxyphenyl) cyclohexanone (19.6% yield).

Workup

  1. concentrationAfter concentrating the reaction solution under reduced pressure
  2. additionan aqueous ammonium chloride solution was added
  3. extractionextraction
  4. washAfter washing the organic layer with saturated saline, it
  5. dry with materialwas dried with anhydrous magnesium sulfate
  6. customThe crude product obtained
  7. distillationfrom distilling off the solvent under reduced pressure
  8. customwas separated
  9. custompurified by silica gel chromatography (n-hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-66bdddf4526a484d84c24bb487f1d83f
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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