Diethyl Ether → 2-(4-oxocyclohexyl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 400177Notes

Reaction equation

HRID 400177 reaction equation
[C:1]1(=[O:18])[N:5]([CH:6]2[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]2)[C:4](=[O:13])[C:3]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:2]12.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(OCC)C>ClCCl>[C:4]1(=[O:13])[N:5]([CH:6]2[CH2:7][CH2:8][C:9](=[O:12])[CH2:10][CH2:11]2)[C:1](=[O:18])[C:2]2=[CH:17][CH:16]=[CH:15][CH:14]=[C:3]12

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 288726trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dioneHCID 178418287HCID 178418287, compound

Product 1

HCID 119983912-(4-oxocyclohexyl)-2,3-dihydro-1H-isoindole-1,3-dioneYield 90.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-phthalimido cyclohexanol (7.1 g, 0.029 mole) in dichloromethane (250 ml) was treated with pyridinium chlorochromate (8.6 g, 0.04 mole) and the resulting dark mixture was stirred at room temperature overnight. Diethyl ether (50 ml) was added and the mixture filtered through keiselguhr. The filtrate was concentrated in vacuo and the residue purified by column chromatography (SiO2 ; CHCl3 /EtOAc) to give 4-phthalimido cyclohexanone as a white solid (6.4 g).

Workup

  1. filtrationthe mixture filtered through keiselguhr
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue purified by column chromatography (SiO2 ; CHCl3 /EtOAc)

Sources & evidence

ORD record
ord-71cdb53c1c884e839ff89995aa90cdc1
Source dataset
uspto-grants-1998_10
Patent number
US05827871

Reaction notes

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