Water → 2-[3-(4-Acetylphenoxy)propyl]-1H-isoindole-1,3(2H)-dione

HRID 1732485Notes

Reaction equation

HRID 1732485 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][CH:7]=1.[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.[K].O>CN(C)C=O>[C:15]1(=[O:25])[N:19]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][CH:7]=2)[C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12

Participants

5

Reactant 3

HCID 962WaterHCID 10061000HCID 10061000, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 203065292-[3-(4-Acetylphenoxy)propyl]-1H-isoindole-1,3(2H)-dioneYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

p-(3-Bromopropoxy)acetophenone (5.14 g.) and potassium phthalimide (3.75 g.) were dissolved in anhydrous N,N-dimethylformamide (50 ml.), and the solution was stirred at 70° C. for 2.5 hours. After the reaction mixture was allowed to cool, water (300 ml.) was poured thereto. The aqueous solution was extracted three times with ethyl acetate, and the extract was washed with ethyl acetate and then dried over magnesium sulfate. The ethyl acetate was removed by evaporation from the solution under reduced pressure, and the resultant residue was treated with ether to give p-(3-phthalimidopropoxy)acetophenone (5.75 g.).

Workup

  1. temperatureto cool
  2. extractionThe aqueous solution was extracted three times with ethyl acetate
  3. washthe extract was washed with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. customThe ethyl acetate was removed by evaporation from the solution under reduced pressure
  6. additionthe resultant residue was treated with ether

Sources & evidence

ORD record
ord-e8ec19c11ea14c5ba6aa433bde0f7a3d
Source dataset
uspto-grants-1980_12
Patent number
US04237305

Reaction notes

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