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

HRID 1920975Notes

Reaction equation

HRID 1920975 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:7]1[CH2:8][CH2:9][O:10][CH:6]1[C:3]1[CH:4]=[CH:5][S:1][CH:2]=1

Participants

5

Reactant 3

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

Product 1

HCID 3156302-(3-Thienyl)-1,3-dioxolaneYield 91%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of thiophene-3-carboxaldehyde (5.0 g, 44.58 mmole) in benzene (200 mL) was added ethylene glycol (25 mL, 445.8 mmole) and p-toluenesulfonic acid hydrate (848 mg, 4.458 mmole). The mixture was heated to reflux under a Dean-Stark trap. After 18 hr the mixture was cooled to RT, washed with saturated NaHCO3 then with H2O, dried (MgSO4), and concentrated under reduced pressure to give the title compound (6.32 g, 91%) as a light amber oil: 1H NMR (400 MHz, CDCl3) δ 7.42 (s, 1H), 7.32 (m, 1H), 7.16 (m, 1H), 5.91 (s, 1H), 4.12-3.99 (m, 4H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under a Dean-Stark trap
  3. washwashed with saturated NaHCO3
  4. dry with materialwith H2O, dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ca944e6af9954f54b456a9441f8cd46d
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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