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

HRID 1054192Notes

Reaction equation

HRID 1054192 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]=[O:7])=[CH:2]1.[CH2:8](O)[CH2:9][OH:10]>C1(C)C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[O:1]1[CH:5]=[CH:4][C:3]([CH:6]2[O:10][CH2:9][CH2:8][O:7]2)=[CH:2]1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 103513-Furaldehyde

Product 1

HCID 143269962-(Furan-3-yl)-1,3-dioxolaneYield 80%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 1140TolueneSolvent

Procedure

To a solution of furan-3-carbaldehyde (SM1-A, 2 g, 20 mmol) and ethane-1,2-diol (3.72 g, 60 mmol) in toluene (100 ml) was added pyridinium p-toluenesulfonate (PPTS, 50 mg, 0.2 mmol), and the solution was heated at reflux utilizing a Dean-Stark trap. After the theoretical amount of water was collected, the solvent was evaporated, and the residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1) to give product (2-A) (1.8 g, 80%) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ 7.54 (s, 1H), 7.41-7.40 (t, 1H), 6.47-6.46 (d, 1H), 5.85 (s, 1H), 4.09-4.06 (m, 2H), 4.00-3.98 (m, 2H).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux
  3. customAfter the theoretical amount of water was collected
  4. customthe solvent was evaporated
  5. customthe residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-6aed8e0dd3e74fe99dfc67411b7ea740
Source dataset
uspto-grants-2016_07
Patent number
US09394296B2

Reaction notes

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