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

HRID 1627780

Reaction equation

HRID 1627780 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 hydrogenocarbonate. 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 sulphatesulphate and concentrated under reduced pressure to afford the ethyl 3-(2-methyl-1,3-dioxolan-2-yl)propanoate as a colorless oil.

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 hydrogenocarbonate
  5. extractionThe basic layer was extracted with diethylether
  6. washwashed with brine and water
  7. dry with materialThe organic layer was dried over sodium sulphatesulphate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ef41ac51bcf841e29afb641fc0b8899b
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Linked notes

Loading…