Acetic Acid → 3-(4-chlorophenyl)-7-hydroxy-2-isopropyl-4-oxo-4H-chromene-8-carbaldehyde

HRID 14499

反応式

HRID 14499 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([OH:19])=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:20]([CH3:22])[CH3:21])=[CH:4][CH:3]=1.C1N2CN3CN(C2)CN1C3.Cl.[C:34](O)(=[O:36])C>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]([CH:34]=[O:36])[C:13]([OH:19])=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:20]([CH3:22])[CH3:21])=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 162024513-(4-Chlorophenyl)-7-hydroxy-2-isopropyl-chromen-4-one

生成物 1

HCID 866256083-(4-chlorophenyl)-7-hydroxy-2-isopropyl-4-oxo-4H-chromene-8-carbaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 3-(4-chlorophenyl)-7-hydroxy-2-isopropyl-chromen-4-one (12.48 g, 39.6 mmol) and hexamethylenetetramine (39.46 g, 0.28 mol) in acetic acid (250 ml) is stirred at 100° C. for 20 h. After the mixture has cooled to room temperature, the solvent is removed in vacuo to afford a black oily residue. 5M HCl solution (150 ml) is added, and the mixture is heated under reflux for 30 min. The reaction mixture is poured onto ice/water, and the resulting brown solid is isolated by filtration. The solid is taken up in dichloromethane, the mixture is passed through a bed of Celite, and the solvent is evaporated in vacuo. The solid residue is stirred at room temperature with ethyl acetate, filtered and washed with hexane to afford the desired product as a pale brown solid.

後処理

  1. temperatureAfter the mixture has cooled to room temperature
  2. customthe solvent is removed in vacuo
  3. customto afford a black oily residue
  4. temperaturethe mixture is heated
  5. temperatureunder reflux for 30 min
  6. additionThe reaction mixture is poured onto ice/water
  7. customthe resulting brown solid is isolated by filtration
  8. customthe solvent is evaporated in vacuo
  9. stirringThe solid residue is stirred at room temperature with ethyl acetate
  10. filtrationfiltered
  11. washwashed with hexane

出典と根拠

ORDレコード
ord-e03fad2a09ea4f109a4d38cc1e388195
出典データセット
uspto-grants-2010_06
特許番号
US07732435B2

関連ノート

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