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

HRID 1179657Notes

Reaction equation

HRID 1179657 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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 IC 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 at 40° C. yielding the title compound (8.52 g, 69% yield, pink solid).

Workup

  1. temperaturewas heated in a round bottom flask at 170 IC for 2 h
  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 at 40° C.

Sources & evidence

ORD record
ord-afb7ec09caba4664a4cde86267767a51
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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