Acetic Anhydride → 2-Methylbenzoxazole

HRID 616423

Reaktionsgleichung

Reaktionsgleichung von HRID 616423
[CH3:1][C:2]([O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[N+:11]([O-])=O)=O.C(OC(=O)C)(=O)C>[Pd]>[CH3:1][C:2]1[O:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[N:11]=1

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 11890Acetic acid, 2-nitrophenyl ester

Produkt 1

HCID 72252-Methylbenzoxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Reaktionsbedingungen

Temperatur
190 °C

Versuchsvorschrift

An autoclave is charged with 18.1 g. o-nitrophenyl acetate, 2.50 g. 5% palladium-on-carbon, 0.50 g. ferric chloride 25 ml. acetic anhydride and 75 ml. acetic acid, purged with nitrogen, pressurized to 5,000 psig. with carbon monoxide, and heated at 190° C. for 5 hours. Analysis of the reaction mixture by vapor phase chromatography indicates complete conversion of the o-nitrophenyl acetate to 2-methylbenzoxazole. The catalyst is separated by filtration and washed with acetone. The solvents are evaporated and the residual oil is dissolved in ether and the solution is washed with aqueous sodium bicarbonate and water. After evaporation of the ether, the crude product is distilled to obtain 2-methylbenzoxazole, b.p.30 mm. 102°-110° C. The product is identical with an authentic sample of 2-methylbenzoxazole by vapor phase chromatography and infrared spectrum.

Aufarbeitung

  1. additionAn autoclave is charged with 18.1 g
  2. customacetic acid, purged with nitrogen
  3. customThe catalyst is separated by filtration
  4. washwashed with acetone
  5. customThe solvents are evaporated
  6. dissolutionthe residual oil is dissolved in ether
  7. washthe solution is washed with aqueous sodium bicarbonate and water
  8. customAfter evaporation of the ether
  9. distillationthe crude product is distilled

Quellen und Nachweise

ORD-Eintrag
ord-6bb74a9921e94effa29d14873816273d
Quelldatensatz
uspto-grants-1978_02
Patentnummer
US04074046

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