Phthalic Anhydride → trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dione

HRID 525053Notes

Reaction equation

HRID 525053 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.[C:9]1(=O)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[O:10]1>CCO>[OH:8][CH:5]1[CH2:6][CH2:7][CH:2]([N:1]2[C:9](=[O:10])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:18])[CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 812934-Aminocyclohexanol

Product 1

HCID 288726trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dioneYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-aminocyclohexanol (3.9 g, 34 mmol) and isobenzofuran-1,3-dione (4.9 g, 34 mmol, 1.0 eq) in 100 mL of EtOH was heated at reflux for 2 days. EtOH was removed and the residue was purified by column chromatography on silica gel (eluent with DCM) to give 2-(4-hydroxycyclohexyl)isoindoline-1,3-dione as white solid (5.0 g, 59%). MS: m/z 246.0 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 days
  3. customEtOH was removed
  4. customthe residue was purified by column chromatography on silica gel (eluent with DCM)

Sources & evidence

ORD record
ord-8ee7fe3b999b4ac88f10619dd663b145
Source dataset
uspto-grants-2016_05
Patent number
US09340554B2

Reaction notes

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