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

HRID 1683252Notes

Reaction equation

HRID 1683252 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-fec56e42a4ef4a96be0982270dbedda9
Source dataset
uspto-grants-1997_06
Patent number
US05637611

Reaction notes

Loading…