Potassium Iodide → HCID 13630976、化合物

HRID 1981561ノート

反応式

HRID 1981561 の反応式
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Cl)(=[O:15])[CH3:14].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8])(=[O:15])[CH3:14]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 392115-Hydroxy-2-nitrobenzaldehydeHCID 1702851-Hexanol, 6-chloro-, 1-acetate

生成物 1

HCID 13630976HCID 13630976、化合物収率 88%

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 50 g (300 mmol) of 5-hydroxy-2-nitrobenzaldehyde, 59 g (330 mmol) 6-chlorohexanol acetate, 5 g of potassium iodide, and 50 g of potassium carbonate in 500 ml of dry DMF was heated to 100° C. under dry nitrogen for 3 h. The reaction was cooled, filtered and evaporated to a dark oil. The crude product was dissolved in 500 ml of ethyl acetate, and the organic layer was washed twice with 300 ml of saturated sodium carbonate, and twice with 300 ml of brine, dried filtered and evaporated. Distillation (180° C., 0.2 mm) gave a yellow oil which solidified on cooling, to yield 81.5 g (263 mmol, 88%) of 5-(6-acetoxyhexyl)oxy-2-nitrobenzaldehyde, m.p. 42°-43° C.

後処理

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. customevaporated to a dark oil
  4. dissolutionThe crude product was dissolved in 500 ml of ethyl acetate
  5. washthe organic layer was washed twice with 300 ml of saturated sodium carbonate
  6. dry with materialtwice with 300 ml of brine, dried
  7. filtrationfiltered
  8. customevaporated
  9. distillationDistillation (180° C., 0.2 mm)
  10. customgave a yellow oil which
  11. temperatureon cooling

出典と根拠

ORDレコード
ord-8bfd1f2776ba4b10818822c6111e55f9
出典データセット
uspto-grants-1986_06
特許番号
US04593029

反応ノート

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