2-(Chloroethoxy)ethanol → 2-(2-(2-Hydroxyethoxy)ethyl)-1H-isoindole-1,3(2H)-dione

HRID 1067187Notes

Reaction equation

HRID 1067187 reaction equation
Cl[CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].[C:8]1(=[O:18])[NH:12][C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12.[K]>CN(C)C=O>[C:8]1(=[O:18])[N:12]([CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7])[C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12

Participants

4

Reactant 2

HCID 123612-(Chloroethoxy)ethanolHCID 24194345Phthalimide potassium salt

Product 1

HCID 27554062-(2-(2-Hydroxyethoxy)ethyl)-1H-isoindole-1,3(2H)-dioneYield 64.17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-(2-chloroethoxy)ethanol 14 (5 mL, 47.4 mmol) in N,N-dimethylformamide (35 mL) was added potassium phthalimide 2 (8.8 g, 47.51 mmol), and the reaction mixture was stirred for 20 h at 70° C. The mixture was concentrated and then diluted with dichloromethane (300 mL), and the organic layer was washed with water, dried, and concentrated. The residue was purified by flash column chromatography (3:2 to 2:3 hexane-ethyl acetate) to give compound 15 as a white solid (7.15 g, 64.17%) having an RF of 0.12 (solvent 3:2 hexane-ethyl acetate). See FIG. 9.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with dichloromethane (300 mL)
  3. washthe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (3:2 to 2:3 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-16131ecb169349579038d3d921c6c36c
Source dataset
uspto-grants-2001_06
Patent number
US06248568B1

Reaction notes

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