Potassium Iodide → 3-(3-(1,3-Dioxoisoindolin-2-yl)propoxy)benzaldehyde

HRID 704909Notes

Reaction equation

HRID 704909 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].[C:16](=[O:19])([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH:9]([C:8]1[CH:11]=[C:16]([CH:13]=[CH:14][CH:7]=1)[O:19][CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15])=[O:10]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 21611N-3-Bromopropylphthalimide

Product 1

HCID 128106403-(3-(1,3-Dioxoisoindolin-2-yl)propoxy)benzaldehydeYield 188.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

m-Hydroxybenzaldehyde (12.2 g), N-(3-bromopropyl)phthalimide (26.8 g), anhydrous potassium carbonate (13.8 g) and potassium iodide (1.7 g) were suspended in acetonitrile (600 ml), and the suspension was heated under reflux for 18 hours. After cooling, the precipitate was removed, and the solvent was evaporated under reduced pressure. The residue was distributed between benzene and water. The organic layer was washed successively with a 1N aqueous NaOH solution, water and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 29.16 g (yield 94%) of N-[3-(3-formylphenoxy)propyl]phthalimide as crystals.

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder reflux for 18 hours
  3. temperatureAfter cooling
  4. customthe precipitate was removed
  5. customthe solvent was evaporated under reduced pressure
  6. washThe organic layer was washed successively with a 1N aqueous NaOH solution, water
  7. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4e880a59fd544db1ae90e99ed59755dd
Source dataset
uspto-grants-1991_01
Patent number
US04988828

Reaction notes

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