2-{4-[1-(2-Methylphenyl)-1-hydroxymethyl]phenyl}-4,4-dimethyl-2-oxazoline → 2-[4-(2-Methylbenzoyl)phenyl]-4,4-dimethyl-2-oxazoline

HRID 1870433Notes

Reaction equation

HRID 1870433 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][CH2:18][C:19]([CH3:22])([CH3:21])[N:20]=2)=[CH:12][CH:11]=1)[OH:9]>[O-2].[O-2].[Mn+4].ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:11]=[CH:12][C:13]([C:16]2[O:17][CH2:18][C:19]([CH3:22])([CH3:21])[N:20]=2)=[CH:14][CH:15]=1)=[O:9]

Participants

4

Reactant 1

HCID 180010162-{4-[1-(2-Methylphenyl)-1-hydroxymethyl]phenyl}-4,4-dimethyl-2-oxazoline

Product 1

HCID 180010212-[4-(2-Methylbenzoyl)phenyl]-4,4-dimethyl-2-oxazolineYield 96%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

2-{4-[1-(2-Methylphenyl)-1-hydroxymethyl]phenyl}-4,4-dimethyl-2-oxazoline (3.0 g), manganese dioxide (20 g) and dichloromethane (50 ml) are mixed at room temperature. The mixture is stirred at room temperature for two hours, and refluxed for three hours. The insoluble materials are removed by filtration through celite, and washed with chloroform, and the mother liquor is concentrated to give 2-[4-(2-methylbenzoyl)phenyl]-4,4-dimethyl-2-oxazoline (2.86 g) as pale yellow oil.

Workup

  1. temperaturerefluxed for three hours
  2. customThe insoluble materials are removed by filtration through celite
  3. washwashed with chloroform
  4. concentrationthe mother liquor is concentrated

Sources & evidence

ORD record
ord-999d1a58378247ff931c7f637f7cf4fe
Source dataset
uspto-grants-2000_08
Patent number
US06096735

Reaction notes

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