Anisole → (4-methoxyphenyl)(naphthalen-2-yl)methanone

HRID 1857122Notes

Reaction equation

HRID 1857122 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[C:19](Cl)=[O:20].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:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[C:19]([C:4]1[CH:5]=[CH:6][C:1]([O:7][CH3:8])=[CH:2][CH:3]=1)=[O:20]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 752462-Naphthoyl chlorideHCID 2733225Ytterbium triflate

Product 1

HCID 267822(4-methoxyphenyl)(naphthalen-2-yl)methanoneYield 31.2%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To commercially available nitromethane (10 ml) were added commercially available anisole (1.081 g), commercially available 2-naphthoyl chloride (1.906 g) and commercially available ytterbium(III) trifluoromethanesulfonate (620 mg), and the admixture was stirred at 60° C. for 8 hours. The reaction mixture was partitioned between water and chloroform, and the chloroform layer was then dried with anhydrous magnesium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate to obtain 817 mg of the title compound (yield: 31%).

Workup

  1. customThe reaction mixture was partitioned between water and chloroform
  2. dry with materialthe chloroform layer was then dried with anhydrous magnesium sulfate
  3. customAfter removing the solvent
  4. distillationby reduced-pressure distillation
  5. customthe resulting residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-a7475c77b5c14a6fb2d3fdc80a28cc19
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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