Pyridine → Ethanone, 2-(acetyloxy)-1-phenyl-

HRID 8191

Reaction equation

HRID 8191 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].N1C=CC=CC=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>CN(C)C1C=CN=CC=1.ClCCl>[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][O:1][C:17](=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 222851Ethanone, 2-(acetyloxy)-1-phenyl-

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-hydroxyaceto-phenone (10 g, 73.4 mmol), pyridine (17.4 g, 220.2 mmol), dichloromethane (734 mL), 3 crystals of 4-dimethylaminopyridine is cooled to −78° C. To this solution is added acetic anhydride (13.9 mL, 146.9 mmol) then warmed to room temperature and stirred for 18 h. The mixture is washed with water (200 mL) and brine (200 mL) then dried over sodium sulfate. The mixture is filtered and concentrated in vacuo to yield the title compound, 13 g (99%), as a colorless liquid.

Workup

  1. washThe mixture is washed with water (200 mL) and brine (200 mL)
  2. dry with materialthen dried over sodium sulfate
  3. filtrationThe mixture is filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a2ba70e58064169870e248f2da8307c
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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