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

HRID 867931Notes

Reaction equation

HRID 867931 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

3-Methyl-2-thiophenecarboxaldehyde (12 g), 1,2-ethanediol (20 ml) and a trace of toluene-p-sulphonic acid were heated at reflux in toluene (250 ml) under Dean and Stark conditions for 4 h. The reaction mixture was cooled and washed with 5% aqueous sodium carbonate solution and water. The toluene solution was evaporated to give an oil which was distilled to give the title compound as a pale yellow oil (14.5 g) b.p. 95°/0.1 mm.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with 5% aqueous sodium carbonate solution and water
  3. customThe toluene solution was evaporated
  4. customto give an oil which
  5. distillationwas distilled

Sources & evidence

ORD record
ord-2026b163e94b4de39571e8771f45461e
Source dataset
uspto-grants-1988_10
Patent number
US04777179

Reaction notes

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