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

HRID 1892513Notes

Reaction equation

HRID 1892513 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-dioxolaneYield 82.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-methylthiophene-2-carbaldehyde (3.53 g, 28.0 mmol) in toluene (75 ml) were added ethylene glycol (31.2 ml, 560 mmol) and a catalytic amount of para toluenesulfonic acid. The mixture was heated under reflux for 17 hr while separating generated water using Dean-Stark trap. The reaction mixture was cooled to room temperature, washed with saturated aqueous sodium hydrogen carbonate and saturated brine, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Merck 7734 80 g, ethyl acetate:hexane=1:10) to give 2-(3-methylthiophen-2-yl)-1,3-dioxolane (3.93 g, 23.1 mmol, yield 82.5%) as a pale-yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 17 hr
  3. customwhile separating
  4. washwashed with saturated aqueous sodium hydrogen carbonate and saturated brine
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (Merck 7734 80 g, ethyl acetate:hexane=1:10)

Sources & evidence

ORD record
ord-12d65a631ee349438bf96b3c568d5f76
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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