Ethylene Glycol → HCID 12688986, compound

HRID 1725564Notes

Reaction equation

HRID 1725564 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH:5]([CH3:9])[C:6](=[O:8])[CH3:7])[CH3:2].[CH2:11](O)[CH2:12][OH:13].O>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:3][C:4](=[O:10])[CH:5]([C:6]1([CH3:7])[O:13][CH2:12][CH2:11][O:8]1)[CH3:9])[CH3:2]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 701Ethyl 2-methylacetoacetateHCID 962Water

Product 1

HCID 12688986HCID 12688986, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-methyl-3-oxo-butyric acid ethyl ester (50 g, 0.347 mol), ethylene glycol (65 g, 1.05 mol) and p-toluenesulfonic acid monohydrate (0.2 g) in anhydrous toluene (200 mL) was refluxed using a Dean-Stark trap until the theoretical amount of water (6.3 mL) was collected. After cooling, the mixture was extracted with saturated bicarbonate solution (100 mL), water (100 mL×5), and brine (100 mL×2). After drying with sodium sulfate, filtration, and concentration on a rotary evaporator, the product was purified by distillation (fraction with b.p. 74-76° C./2 mm Hg) to yield 47.12 g (72%) of 2-(2-methyl-[1,3]dioxolan-2-yl)-propionic acid ethyl ester.

Workup

  1. temperaturewas refluxed
  2. customwas collected
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with saturated bicarbonate solution (100 mL), water (100 mL×5), and brine (100 mL×2)
  5. dry with materialAfter drying with sodium sulfate, filtration, and concentration on a rotary evaporator
  6. distillationthe product was purified by distillation (fraction with b.p. 74-76° C./2 mm Hg)

Sources & evidence

ORD record
ord-ebb3eb0a32a641169a78e94107e178e7
Source dataset
uspto-grants-2009_02
Patent number
US07491728B2

Reaction notes

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