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

HRID 2087002Notes

Reaction equation

HRID 2087002 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH2:4][CH2:3]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl.CCOCC>[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 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 65.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(4-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione (3.10 g, 12.6 mmol) in CH2Cl2 (25.0 mL) was added to a slurry of PCC (4.10 g, 19.0 mmol) in CH2Cl2 (15.0 mL) and stirred at room temperature for 3.5 hours. The reaction was diluted with Et2O (60.0 mL), decanted and the residue swirled with Et2O (2×40.0 mL). The combined ether layers were filtered through florisil and concentrated in vacuo to dryness, and the residue was recrystallized from ethyl acetate/hexane to give 2.01 g (65%) of 2-(4-oxocyclohexyl)-1H-isoindole-1,3(2H)-dione as colorless needles: mp 140.3-142.1° C.; 1H NMR (400 MHz, CDCl3) δ 7.84, 7.74, 4.64, 2.72, 2.54, 2.09; 13C NMR (100 MHz, CDCl3) δ 208.9, 168.1, 134.1, 131.9, 123.3, 48.4, 39.9, 28.6; IR (mull) 3062, 3031, 2958, 2949, 2919, 2885, 1775, 1762, 1721, 1708, 1611, 1465, 1436, 1419, 1393, 1379, 719 cm−1; HRMS (FAB) calcd for C14H14NO3: 244.0974, found 244.0976; Anal. Calcd for C-14H14NO3: C, 69.12; H, 5.39; N, 5.76. Found: C, 68.87; H, 5.47; N, 5.73.

Workup

  1. customdecanted
  2. filtrationThe combined ether layers were filtered through florisil
  3. concentrationconcentrated in vacuo to dryness
  4. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c62f8f8131c24add9396d4d3daa705ee
Source dataset
uspto-grants-2004_04
Patent number
US06727274B2

Reaction notes

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