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Methane → cis-2-(4-Hydroxy-phenyl)hexahydroisoindole-1,3-dione

HRID 1179663
ノート
印刷プレビュー

反応式

HRID 1179663 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C@@H:9]12[C:18](=O)[O:17][C:15](=[O:16])[C@@H:10]1[CH2:11][CH2:12][CH2:13][CH2:14]2.C>C(O)C>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([N:1]2[C:15](=[O:16])[C@H:10]3[C@H:9]([CH2:14][CH2:13][CH2:12][CH2:11]3)[C:18]2=[O:17])=[CH:3][CH:4]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 297MethaneHCID 4034-AminophenolHCID 641660Hexahydrophthalic anhydride, cis-

生成物 1

HCID 7035660cis-2-(4-Hydroxy-phenyl)hexahydroisoindole-1,3-dione収率 69.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
170 °C

実験手順

A mixture of 4-aminophenol (5.46 g, 50.0 mmol) and cis-1,2-cyclohexanedicarboxylic anhydride (7.71 g, 50.0 mmol) was heated in a round bottom flask at 170° C. for 2 h. After cooling to room temperature the solid material was dissolved in hot ethanol (200 ml), activated charcoal was added and the solution was heated at reflux for 1 h. The solid material was removed by hot filtration. The solvent was partially evaporated. The solids were collected by filtration, washed quickly with a small amount of ethanol and dried in vacuo yielding the title compound (8.52 g, 69%, pink solid).

後処理

  1. temperatureAfter cooling to room temperature the solid material
  2. temperaturethe solution was heated
  3. temperatureat reflux for 1 h
  4. customThe solid material was removed by hot filtration
  5. customThe solvent was partially evaporated
  6. filtrationThe solids were collected by filtration
  7. washwashed quickly with a small amount of ethanol
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-2cc04dd1821440859d2b9ca97f21a689
出典データセット
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07279470B2

反応ノート

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