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

HRID 1249968Notes

Reaction equation

HRID 1249968 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. 1H-NMR (200 MHz, CDCl3) δ ppm: 1.40 (6H, s), 2.33 (3H, s), 4.14 (2H, s), 7.12-7.54 (4H, m), 7.76-7.92 (2H, m), 7.95-8.14 (2H, m).

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-4bd43e90db4c425189004185c5796bdc
Source dataset
uspto-grants-2002_01
Patent number
US06335327B1

Reaction notes

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