N-Hydroxyphthalimide → 2-(3-Methylbut-2-enyloxy)isoindoline-1,3-dione

HRID 2226157Notes

Reaction equation

HRID 2226157 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18].Br[CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23]>CS(C)=O>[CH3:23][C:22]([CH3:24])=[CH:21][CH2:20][O:7][N:8]1[C:9](=[O:18])[C:10]2=[CH:17][CH:16]=[CH:15][CH:14]=[C:11]2[C:12]1=[O:13]

Participants

5

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-

Product 1

HCID 222862302-(3-Methylbut-2-enyloxy)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium carbonate (7.55 g, 54.6 mmol) was added to a solution of N-hydroxyphthalimide (13.93 g, 85.4 mmol) in 150 mL of DMSO to give a wine-red colored solution. 4-Bromo-2-methyl-2-butene (20 g, 134 mmol) was added to the solution dropwise and the reaction was stirred for 16 hours at room temperature. The reaction was poured into 600 mL of ice water to give a white crystalline solid. The crude crystalline product was filtered, washed with ice water, and air dried. The crystalline product was recrystallized from ethanol to give 15.7 g, mp 97°-98° C.

Workup

  1. customto give a wine-red colored solution
  2. customto give a white crystalline solid
  3. filtrationThe crude crystalline product was filtered
  4. washwashed with ice water, and air
  5. customdried
  6. customThe crystalline product was recrystallized from ethanol
  7. customto give 15.7 g, mp 97°-98° C.

Sources & evidence

ORD record
ord-26c2d45c68e74ca08824fb0d93e4bfb9
Source dataset
uspto-grants-1994_09
Patent number
US05346911

Reaction notes

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