Acetonitrile → Ethanone, 2-[[(4-methylphenyl)sulfonyl]oxy]-1-(2-naphthalenyl)-

HRID 902200Notes

Reaction equation

HRID 902200 reaction equation
C(#N)C.[CH3:4][C:5]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)=[O:6].OI(C1C=CC=CC=1)[O:19][S:20]([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>C(OCC)(=O)C>[S:20]([O:22][CH2:4][C:5]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)=[O:6])([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:21])=[O:19]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 71222-AcetylnaphthaleneHCID 325434[Hydroxy(tosyloxy)iodo]benzene

Product 1

HCID 10783345Ethanone, 2-[[(4-methylphenyl)sulfonyl]oxy]-1-(2-naphthalenyl)-Yield 68.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetonitrile solution (40 mL) containing 2-acetonaphthone (1.70 g, 9.99 mmol) and [hydroxyl(tosyloxy)iodo]benzene (4.00 mg, 10.2 mmol) was heated under ref lux for 3 hours. The reaction mixture was cooled, and ethyl acetate was added thereto. The reaction solution was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo to remove the solvent to obtain the title compound (2.33 g, 68.5%).

Workup

  1. temperaturewas heated under ref lux for 3 hours
  2. temperatureThe reaction mixture was cooled
  3. washThe reaction solution was washed with saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto remove the solvent

Sources & evidence

ORD record
ord-6bdc437cfd1a463dbf57df0ae3c50752
Source dataset
uspto-grants-2008_04
Patent number
US07365079B2

Reaction notes

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