Ethylene Glycol → Ethyl acetoacetate ethyleneglycol ketal

HRID 2352386Notes

Reaction equation

HRID 2352386 reaction equation
C1C=CC=CC=1.[C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:9])[CH3:8].[CH2:16](O)[CH2:17][OH:18]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:16]1[CH2:17][O:18][C:7]([CH3:8])([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[O:9]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 241BenzeneHCID 8868Ethyl Acetoacetate

Product 1

HCID 80865Ethyl acetoacetate ethyleneglycol ketalYield 92%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

Benzene (50 cc), ethyl acetylacetate (30 g, 231 mmol) and ethylene glycol (16 g), followed by p-toluenesulphonic acid (0.5 g), are introduced into a round-bottomed flask fitted with a Dean and Stark apparatus. The mixture is heated under reflux while the azeotrope is distilled off for 2 hours 30 minutes. After the removal of benzene, ethyl 3,3-ethylenedioxybutanoate (37 g) is obtained (B.P.12 =98° C.).

Workup

  1. additionare introduced into a round-bottomed flask
  2. customfitted with a Dean and Stark apparatus
  3. temperatureThe mixture is heated
  4. temperatureunder reflux while the azeotrope
  5. distillationis distilled off for 2 hours 30 minutes
  6. customAfter the removal of benzene

Sources & evidence

ORD record
ord-0a867b0b1719436abb0488edbcac32a9
Source dataset
uspto-grants-1989_10
Patent number
US04876370

Reaction notes

Loading…