o-Vanillin → Benzaldehyde, 3-methoxy-2-(4-nitrophenoxy)-

HRID 2226896

반응식

HRID 2226896 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[O:11]=[CH:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:16]([O:17][CH3:18])[C:14]=1[OH:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:18][O:17][C:16]1[C:14]([O:15][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)=[C:13]([CH:21]=[CH:20][CH:19]=1)[CH:12]=[O:11]

참가 물질

5

반응물 3

HCID 8991o-VanillinHCID 9590p-FluoronitrobenzeneHCID 11430Potassium Carbonate

생성물 1

HCID 22402430Benzaldehyde, 3-methoxy-2-(4-nitrophenoxy)-수율 71%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of 14.10 g (0.10 mole) of 4-fluoronitrobenzene, 16.40 g (0.10 mole) of o-vanillin, 30 g of powdered potassium carbonate, and 40 mL of DMF is heated with stirring to the boiling point. After 10 minutes the mixture is cooled to 100° C. and 300 mL of ice water is added. Petroleum ether (200 mL) is added and the entire mixture filtered and the cake is washed with 200 mL of water and then 200 mL of petroleum ether. The damp cake slurried in 100 mL of methanol and filtered; wt 19.50 g (71% yield); mp 130°-131° C.; mass spectrum (DEI), 273 (M+).

후처리

  1. temperatureis heated
  2. filtrationthe entire mixture filtered
  3. washthe cake is washed with 200 mL of water
  4. filtrationfiltered

출처 및 근거

ORD 기록
ord-e4e10bcbf79a4eefb4eb06d7598c3e98
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05350757

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