Phthalimide → 3-(3-(1,3-Dioxoisoindolin-2-yl)propyl)benzaldehyde

HRID 1967673Notes

Reaction equation

HRID 1967673 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[OH2:12].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16](S(O)(=O)=O)=[CH:15][CH:14]=1.[CH3:24][C:25]([CH3:27])=O.O>>[O:6]=[C:4]1[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:1](=[O:11])[N:5]1[CH2:16][CH2:17][CH2:18][C:13]1[CH:23]=[C:25]([CH:27]=[CH:15][CH:14]=1)[CH:24]=[O:12]

Participants

4

Reactant 3

HCID 6809PhthalimideHCID 521998p-Toluenesulfonic acid monohydrateHCID 18366337Propan-2-one--water (1/1)

Product 1

HCID 577664653-(3-(1,3-Dioxoisoindolin-2-yl)propyl)benzaldehyde

Procedure

To a solution of phthalimide 50 (5.66 g, 16.67 mmol) in acetone-water (5:1, 50 mL) was added p-toluenesulfonic acid hydrate (0.2116 g, 1.11 mmol). The mixture was stirred for 3 h then concentrated under reduced pressure. The residue was partitioned between EtOAc and water and the combined organics were washed with brine, dried over MgSO4 and concentrated under reduced pressure to give phthalimide 29 as a white solid. Yield (4.48 g, 92%). The NMR data was consistent with data reported above.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue was partitioned between EtOAc and water
  3. washthe combined organics were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c434441ead334fdcb04d6983dc5bbd51
Source dataset
uspto-grants-2013_04
Patent number
US08420863B2

Reaction notes

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