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

HRID 2120605

Reaction equation

HRID 2120605 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-05351556deb44d278080e5c583d27237
Source dataset
uspto-grants-2004_02
Patent number
US06693098B2

Linked notes

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