o-nitrophenyl benzoate → Benzoxazole, 2-phenyl-

HRID 616424Notes

Reaction equation

HRID 616424 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-])=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd]>[C:2]1([C:1]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:16]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 294244o-nitrophenyl benzoate

Product 1

HCID 70030Benzoxazole, 2-phenyl-

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
190 °C

Procedure

An autoclave is charged with 2.43 g. o-nitrophenyl benzoate, 0.50 g. 5% palladium-on-carbon, 0.25 g. ferric chloride and 20 ml. of acetonitrile, purged with nitrogen, pressurized to 5,000 psig. with carbon monoxide, and heated at 190° C. for 6 hours. Analysis of the reaction mixture by vapor phase chromatography shows that the major component (87%) is 2-phenylbenzoxazole and a minor component is 3-benzoyl-2-benzoxazolinone. The catalyst is removed and the solvent is evaporated. Chromatography of the residual oil on alumina yields 2-phenylbenzoxazole, melting point 100°-102° C., identical with an authentic sample by mixed melting point and infrared spectrum.

Workup

  1. additionAn autoclave is charged with 2.43 g
  2. customof acetonitrile, purged with nitrogen
  3. customThe catalyst is removed
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-76e2ec5b5d594836ac0c45449ee94ad8
Source dataset
uspto-grants-1978_02
Patent number
US04074046

Reaction notes

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