Ethylene Glycol → 2-(3-Methylthiophen-2-yl)-1,3-dioxolane

HRID 9655

Reaction equation

HRID 9655 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8].[CH2:9](O)[CH2:10][OH:11].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]1[O:11][CH2:10][CH2:9][O:8]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 799113-Methyl-2-thiophenecarboxaldehyde

Product 1

HCID 129265222-(3-Methylthiophen-2-yl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-methylthiophene carboxaldehyde (6.8 g), ethylene glycol (10 ml) and p-toluenesulfonic acid (0.30 g) in toluene (125 ml) was heated at reflux for 18 hours. The reaction mixture was cooled; extracted with 2M aqueous sodium carbonate and then dried with brine and over magnesium sulfate. Analysis of the crude product indicated that the reaction was incomplete so the crude material was re-subjected to the ketalisation conditions as outlined above. The crude material isolated after reprocessing was distilled under reduced pressure (1 mmHg) to give the title compound as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with 2M aqueous sodium carbonate
  5. dry with materialdried with brine and over magnesium sulfate
  6. customThe crude material isolated
  7. distillationafter reprocessing was distilled under reduced pressure (1 mmHg)

Sources & evidence

ORD record
ord-74b822405f8e419aaae0449610e9ed3b
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Linked notes

Loading…