Ethylene Glycol → N-[6-(2-Methyl-1,3-dioxolan-2-yl)hexyl]phthalimide

HRID 1164495Notes

Reaction equation

HRID 1164495 reaction equation
[O:1]=[C:2]([CH3:20])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19].[CH2:21](O)[CH2:22][OH:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:20][C:2]1([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][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])[O:23][CH2:22][CH2:21][O:1]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 205113062-(7-Oxooctyl)isoindoline-1,3-dione

Product 1

HCID 20511312N-[6-(2-Methyl-1,3-dioxolan-2-yl)hexyl]phthalimide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 142.0 g (0.52 mole) of N-(7-oxooctyl)phthalimide, 60 ml of ethylene glycol, 5.80 g of p-toluenesulfonic acid and 290 ml of benzene was refluxed overnight using a Dean-Stark trap to collect the azeotrope. The reaction was cooled, treated with 2 N NaOH solution, the organic layer separated, dried over anhydrous potassium carbonate, filtered and stripped to give 125.25 g of orange oil, 76% pure by gc (SE-30, 90°-280°@16°/min).

Workup

  1. temperaturewas refluxed overnight
  2. customto collect the azeotrope
  3. temperatureThe reaction was cooled
  4. additiontreated with 2 N NaOH solution
  5. customthe organic layer separated
  6. dry with materialdried over anhydrous potassium carbonate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-68ba29fde0bd46918092e069cfd91ec4
Source dataset
uspto-grants-1983_01
Patent number
US04370335

Reaction notes

Loading…