Succinimide → 1-(2-Hydroxy-3-(phenoxy)propyl)succinimide

HRID 544418Notes

Reaction equation

HRID 544418 reaction equation
[O:1]1[CH2:11][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:12]1(=[O:18])[NH:16][C:15](=[O:17])[CH2:14][CH2:13]1>C(O)C.N1C=CC=CC=1>[C:15]1(=[O:17])[N:16]([CH2:11][CH:2]([OH:1])[CH2:3][O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:12](=[O:18])[CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 11439SuccinimideHCID 31217Phenyl glycidyl ether

Product 1

HCID 2927851-(2-Hydroxy-3-(phenoxy)propyl)succinimideYield 72.2%

Reagents, catalysts & solvents 2

HCID 702EthanolCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 15 gm (0.1 mole) of 2,3-epoxypropoxybenzene (prepared as described in Example I) and 9.9 gm (0.1 mole) of succinimide in 100 mL ethanol having 10 drops of pyridine was heated to reflux for 4 hours. After standing 24 hours at room temperature a white crystalline product separated. This material was collected, air-dried and recrystallized from 700 mL ethyl acetate:hexane (6:1) to give 18 gm (72%) of white crystals: mp 130°. The NMR spectrum and the elemental analyses were consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. customa white crystalline product separated
  4. customThis material was collected
  5. customair-dried
  6. customrecrystallized from 700 mL ethyl acetate:hexane (6:1)

Sources & evidence

ORD record
ord-8dd94187926b4374803dc22b6c81e990
Source dataset
uspto-grants-1984_05
Patent number
US04450173

Reaction notes

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