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

HRID 1883204Notes

Reaction equation

HRID 1883204 reaction equation
O.[C:2]1(C)[CH:7]=[CH:6][C:5]([S:8](O)(=O)=O)=CC=1.[CH2:13]([OH:16])[CH2:14][OH:15].[C:17]1(C)C=CC=CC=1>>[O:15]1[CH2:14][CH2:13][O:16][CH:17]1[C:7]1[CH:6]=[CH:5][S:8][CH:2]=1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

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

Conditions

Temperature
111 °C

Procedure

Under nitrogen atmosphere, to a solution of 3-thiophene-carboxyaldehyde (9.81 g) in toluene (200 mL) were added p-toluene-sulfonic acid monohydrate (190 mg) and ethylene glycol (6.52 g), and the mixture was stirred at 111° C. for 5 hours. The mixture was cooled to room temperature, washed twice with an aqueous NaHCO3 solution, dried over MgSO4. The solvent was evaporated under reduced pressure to give 3-(1,3-dioxolan-2-yl)thiophene (10.4 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed twice with an aqueous NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8cbf403f32014a5cba15864e21030a37
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

Loading…