2-Propanol, 1,3-diphthalimido- → HCID 23374871, compound

HRID 1653940Notes

Reaction equation

HRID 1653940 reaction equation
[C:1]1(=[O:26])[N:5]([CH2:6][CH:7](O)[CH2:8][N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])[C:4](=[O:21])[C:3]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:2]12.CC(C)=[O:29].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:1]1(=[O:26])[N:5]([CH2:6][CH2:7][C:8]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])=[O:29])[C:4](=[O:21])[C:3]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:2]12

Participants

4

Reactant 2

HCID 971302-Propanol, 1,3-diphthalimido-HCID 131709961Jones' reagent

Product 1

HCID 23374871HCID 23374871, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1,3-diphthalimido-2-hydroxypropane (1.00 g., 2,86 mmol) in 80 mL of acetone was added Jones reagent (chromium trioxide and sulfuric acid) until an orange color persisted. The excess oxidant was removed by the addition of 2-isopropanol until a green color was obtained and the solvents were evaporated under reduced pressure. The residue was partitioned between methylene chloride and water and the layers were separated. The organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated under reduced pressure to give 1,3-diphthalimido-3-oxopropane.

Workup

  1. customThe excess oxidant was removed by the addition of 2-isopropanol until a green color
  2. customwas obtained
  3. customthe solvents were evaporated under reduced pressure
  4. customThe residue was partitioned between methylene chloride and water
  5. customthe layers were separated
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4e42606ba93e48eebebcf349827fdcf3
Source dataset
uspto-grants-1995_04
Patent number
US05405601

Reaction notes

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