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

HRID 1905439Notes

Reaction equation

HRID 1905439 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.O.S(=O)(=O)(O)O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[K+].[K+]>C(Cl)(Cl)Cl>[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

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 24502Potassium DichromateHCID 288726trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dione

Product 1

HCID 119983912-(4-oxocyclohexyl)-2,3-dihydro-1H-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

95 g (0.388 Mol) of 4-(phthalimido)-cyclohexanol are dissolved in 600 ml of chloroform and, after the addition of 450 ml of water and 120 ml of sulfuric acid, 90 g (0.3 Mol) of potassium dichromate are added in batches. The internal temperature of the mixture is maintained at between 25° and 30° C. by slight cooling. The mixture is stirred for a further 3 hours, then the chloroform phase is separated off and the mixture extracted twice more with chloroform. After drying and concentration of the extracts 82 g (86.9% of theory) are obtained.

Workup

  1. additionare added in batches
  2. temperatureThe internal temperature of the mixture is maintained at between 25° and 30° C. by slight cooling
  3. customthe chloroform phase is separated off
  4. extractionthe mixture extracted twice more with chloroform
  5. customAfter drying
  6. customconcentration of the extracts 82 g (86.9% of theory) are obtained

Sources & evidence

ORD record
ord-7776c625248a4aa882c807237e3e3160
Source dataset
uspto-grants-1989_06
Patent number
US04843086

Reaction notes

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