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

HRID 2426352Notes

Reaction equation

HRID 2426352 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.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

5

Reactant 2

HCID 174Ethylene GlycolHCID 10883Ethyl levulinate

Product 1

HCID 70332Ethyl 2-methyl-1,3-dioxolane-2-propionateYield 91.5%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of ethyl levulinate (58.35 g, 400.0 mmol), ethylene glycol (75.36 g, 1.21 mol), pyridinium p-toluenesulfonate (100 mg) and toluene (200 mL) was heated at reflux under a Dean Stark trap. The trap was emptied every 15 minutes during the reaction until approximately 200 mL of reaction volatiles had been removed. The remaining toluene was removed under reduced pressure, and the resulting oil was partitioned between ethyl acetate (200 mL) and water (50 mL). The organic layer was separated and washed sequentially with water (2×50 mL), saturated aqueous sodium bicarbonate (50 mL), and brine (50 mL); dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 68.9 g of ethyl 3-(2-methyl-1,3-dioxolan-2-yl)propanoate as a light yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a Dean Stark trap
  3. customThe trap was emptied every 15 minutes during the reaction until approximately 200 mL of reaction volatiles
  4. customhad been removed
  5. customThe remaining toluene was removed under reduced pressure
  6. customthe resulting oil was partitioned between ethyl acetate (200 mL) and water (50 mL)
  7. customThe organic layer was separated
  8. washwashed sequentially with water (2×50 mL), saturated aqueous sodium bicarbonate (50 mL), and brine (50 mL)
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1e41ffda8a5e4a30a22c7d724adf2c9b
Source dataset
uspto-grants-2011_06
Patent number
US07968563B2

Reaction notes

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