Anisole → Cyclohexyl(4-methoxyphenyl)methanone

HRID 1857209Notes

Reaction equation

HRID 1857209 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:9]1([C:15](Cl)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[N+](C)([O-])=O>[CH:9]1([C:15]([C:4]2[CH:5]=[CH:6][C:1]([O:7][CH3:8])=[CH:2][CH:3]=2)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 75938Cyclohexanecarbonyl chlorideHCID 2733225Ytterbium triflate

Product 1

HCID 345014Cyclohexyl(4-methoxyphenyl)methanoneYield 51%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To commercially available nitromethane (5 ml) were added commercially available anisole (0.5 ml), commercially available cyclohexanecarbonyl chloride (0.63 ml) and commercially available ytterbium(III) trifluoromethanesulfonate (288 mg), and the admixture was stirred at 60° C. for 3 hours. The reaction mixture was partitioned between water and chloroform, and the chloroform layer was washed with saturated aqueous sodium hydrogen carbonate and brine and then dried with anhydrous sodium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by chromatography on silica gel eluting with chloroform to obtain 517 mg of the title compound (yield: 51%).

Workup

  1. customThe reaction mixture was partitioned between water and chloroform
  2. washthe chloroform layer was washed with saturated aqueous sodium hydrogen carbonate and brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. customAfter removing the solvent
  5. distillationby reduced-pressure distillation
  6. customthe resulting residue was purified by chromatography on silica gel eluting with chloroform

Sources & evidence

ORD record
ord-060eeeef93fd408dbb25c5ae262a79cb
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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