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

HRID 260071

反応式

HRID 260071 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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 is filtered and the cake is washed with 200 mL of water and then 200 mL of petroleum ether. The damp cake is slurried in 100 mL of methanol and filtered; wt 19.50 g (71% yield); mp 130°-131° C.; mass spectrum (DEI), 273 (M+).

後処理

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

出典と根拠

ORDレコード
ord-a182eebdcb214c58be24a004df17ef86
出典データセット
uspto-grants-1996_06
特許番号
US05525614

関連ノート

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