Ethylene Oxide → N-(2-Hydroxyethyl)phthalimide

HRID 1657684Notes

Reaction equation

HRID 1657684 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.[CH2:12]1[O:14][CH2:13]1>[Cr].CC(CC(C)C)=O>[OH:14][CH2:13][CH2:12][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

Participants

5

Reactant 2

HCID 6354Ethylene OxideHCID 6809Phthalimide

Product 1

HCID 77499N-(2-Hydroxyethyl)phthalimide

Reagents, catalysts & solvents 2

HCID 23976ChromiumCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

N-2-Hydroxyethyl phthalimide was prepared by allowing 147.2g (1.0 mole) of phthalimide to react in an autoclave with 53.0g (1.20 moles) of ethylene oxide in the presence of 1.47g (1%) of active chromium III tri-2-ethylhexanoate (COT) and 400 ml of methylisobutyl ketone (MiBK) at 160° to 165°C for two hours. On cooling, the N-2-hydroxyethyl phthalimide crystallized and was collected by filtration. A 94.7% yield of the hydroxyethyl imide was obtained. Under identical experimental conditions but in the absence of COT, the starting material was recovered unchanged.

Workup

  1. temperatureOn cooling
  2. customthe N-2-hydroxyethyl phthalimide crystallized
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-b26bf26a63814a5d9ac1feeef127c9d3
Source dataset
uspto-grants-1976_06
Patent number
US03962182

Reaction notes

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