Water → 2-p-Tolylbenzoxazole

HRID 6209

Reaction equation

HRID 6209 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1O.O.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C1(C)C=CC=CC=1>[CH3:9][C:1]1[CH:6]=[CH:5][C:4]([C:7]2[O:8][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 58012-AminophenolHCID 77254-MethylbenzaldehydeHCID 178418268HCID 178418268, compound

Product 1

HCID 700392-p-Tolylbenzoxazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 12 g (0.1 mole) of 4-tolualdehyde and 10.9 g (0.1 mole) of 2-aminophenol in toluene is heated at reflux with azeotropic removal of water. After 20 hours at reflux, the reaction is cooled to room temperature, 44.3 g (0.1 mole) of lead tetraacetate is added, and the mixture is stirred at room temperature overnight. The solids are removed by filtration, and the filtrate is swirled with basic alumina. Removal of the solvent in vacuo affords the solid product which is then purified by recrystallization from benzene.

Workup

  1. temperatureAfter 20 hours at reflux
  2. customThe solids are removed by filtration
  3. customRemoval of the solvent in vacuo
  4. customaffords the solid product which
  5. customis then purified by recrystallization from benzene

Sources & evidence

ORD record
ord-a8c9dc88ef314c6e9a5ee94f173add5d
Source dataset
uspto-grants-1993_09
Patent number
US05247042

Linked notes

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