Ethylene Glycol → Ethyl 2-methyl-1,3-dioxolane-2-propionate

HRID 2276335Notes

Reaction equation

HRID 2276335 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[CH2:2][CH2:3][C:4]([CH3:6])=[O:5].[CH2:11](O)[CH2:12][OH:13].C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>C1(C)C=CC=CC=1>[CH3:6][C:4]1([CH2:3][CH2:2][C:1]([O:8][CH2:9][CH3:10])=[O:7])[O:13][CH2:12][CH2:11][O:5]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 10883Ethyl levulinateHCID 22033616Pyridinium.p-toluenesulfonate

Product 1

HCID 70332Ethyl 2-methyl-1,3-dioxolane-2-propionate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a flask equipped by a Dean-Stark trap, a mixture of ethyl levulinate (28.83 g; 200 mmol), ethylene glycol (37.24 g; 600 mmol) and a catalytic amount of pyridinium para-toluenesulfonic acid in toluene (200 mL) was heated at reflux until the theoretical amount of water was distilled off. After cooling, the mixture was washed with a saturated solution of sodium hydrogen carbonate. The basic layer was extracted with diethylether and the organics were combined, then washed with brine and water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford the ethyl 3-(2-methyl-1,3-dioxolan-2-yl)propanoate as a colorless oil. ESI/APCI(+): 189 (M+H). 1H NMR (CDCl3): δ 4.12 (q, J=7.14 and 14.25 Hz, 2H, CO2CH2CH3); 3.93 (m, 4H, OCH2CH2O); 2.37 (m, 2H, CH2); 2.02 (m, 2H, CH2); 1.32 (s, 3H, CH3); 1.25 (t, J=7.14 Hz, 3H, CO2CH2CH3).

Workup

  1. customIn a flask equipped by a Dean-Stark trap
  2. distillationwas distilled off
  3. temperatureAfter cooling
  4. washthe mixture was washed with a saturated solution of sodium hydrogen carbonate
  5. extractionThe basic layer was extracted with diethylether
  6. washwashed with brine and water
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-39788a9f238d4bf4b70a5cc21cff292e
Source dataset
uspto-grants-2015_09
Patent number
US09132129B2

Reaction notes

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