Ethylene Glycol → 2-(3-Thienyl)-1,3-dioxolane

HRID 1489104Notes

Reaction equation

HRID 1489104 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=[O:7])=[CH:2]1.[CH2:8](O)[CH2:9][OH:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[O:7]1[CH2:8][CH2:9][O:10][CH:6]1[C:3]1[CH:4]=[CH:5][S:1][CH:2]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 681353-ThiophenecarboxaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 3156302-(3-Thienyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 28.04 g (250 mmol) of 3-thiophenecarboxaldehyde, 20.2 g (330 mole) of ethyleneglycol, 10 mg (0.05 mmole) of p-toluenesulfonic acid monohydrate and 25 ml of benzene was heated to reflux untill the calculated amount of water was removed via a Dean-Stark trap (5 hours). The reaction mixture was allowed to cool to room temperature and was washed with 30 ml of saturated NaHCO3 solution. The organic layer was dried over MgSO4 and the solvent was removed by evaporation to give the title compound as a clear colorles oil.

Workup

  1. customwas removed via a Dean-Stark trap (5 hours)
  2. washwas washed with 30 ml of saturated NaHCO3 solution
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-1cf9ed889fe04b538bcc42227905f063
Source dataset
uspto-grants-1997_10
Patent number
US05677320

Reaction notes

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