Acetic Anhydride → 2-Methylbenzoxazole

HRID 616423

반응식

HRID 616423 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 72252-Methylbenzoxazole

시약·촉매·용매 1

HCID 23938Palladium촉매

반응 조건

온도
190 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6bb74a9921e94effa29d14873816273d
출처 데이터셋
uspto-grants-1978_02
특허 번호
US04074046

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