N-(2-hydroxy-2-phenylethyl)acetamide → n-(2-Oxo-2-phenylethyl)acetamide

HRID 1004484Notes

Reaction equation

HRID 1004484 reaction equation
[OH:1][CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][NH:4][C:5](=[O:7])[CH3:6].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[O:1]=[C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][NH:4][C:5](=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 270963N-(2-hydroxy-2-phenylethyl)acetamideHCID 178418287HCID 178418287, compound

Product 1

HCID 226684n-(2-Oxo-2-phenylethyl)acetamideYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(2-hydroxy-2-phenyl-ethyl)-acetamide (7.68 g, 43 mmol), prepared in the previous step, and pyridinium chlorochromate (14.0 g, 65 mmol) in 800 ml of methylene chloride was stirred at room temperature for 5 hours. The organic phase was decanted from a black oily residue in the flask. This black residue was triturated with methylene chloride and then with 10% methanol-methylene chloride. The organic phases were concentrated under reduced pressure and the residue chromatographed on 400 g of silica gel (230-400 mesh) using ethyl acetate-methylene chloride as the eluent. Isolation of the desired component gave N-(2-oxo-2-phenyl-ethyl)-acetamide (4.0 g, 53%) as a white solid. The material was used in the following reaction without additional purification, MS m/e (M+H)+ 178.

Workup

  1. customThe organic phase was decanted from a black oily residue in the flask
  2. customThis black residue was triturated with methylene chloride
  3. concentrationThe organic phases were concentrated under reduced pressure
  4. customthe residue chromatographed on 400 g of silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-94c4313e458c450c83f74169d7548441
Source dataset
uspto-grants-2000_04
Patent number
US06049006

Reaction notes

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