2-Benzylideneamino-4-methylphenol → 2-Phenyl-5-methylbenzoxazole

HRID 970814

Reaction equation

HRID 970814 reaction equation
[CH:1](=[N:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[OH:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.O.O.C([O-])(=O)C.[Mn+3].C([O-])(=O)C.C([O-])(=O)C>[CH3:15][C:13]1[CH:12]=[CH:11][C:10]2[O:16][C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:8][C:9]=2[CH:14]=1

Participants

4

Reactant 1

HCID 112987892-Benzylideneamino-4-methylphenol

Product 1

HCID 819192-Phenyl-5-methylbenzoxazoleYield 93.3%

Reagents, catalysts & solvents 2

HCID 12416832Manganese triacetate dihydrateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-benzylideneamino-4-methylphenol 54 (1.34 g, 6.3 mmol) and manganese (III) acetate dihydrate (3.4 g, 12.7 mmol) in toluene (65 ml) was heated at reflux under an atmosphere of N2 for 1 hr and cooled to room temperature. The mixture was filtered to remove the insoluble manganese salts. The filtrate was evaporated under reduced pressure. The residue was taken up in methylene chloride and purified by filtration to yield 1.23 g 5-methyl-2-phenylbenzoxazole 55.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under an atmosphere of N2 for 1 hr
  3. filtrationThe mixture was filtered
  4. customto remove the insoluble manganese salts
  5. customThe filtrate was evaporated under reduced pressure
  6. filtrationpurified by filtration

Sources & evidence

ORD record
ord-dccdd17e304a420d9312af8ef26f3894
Source dataset
uspto-grants-2007_12
Patent number
US07312230B2

Linked notes

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