Ethylene Glycol → HCID 20087711, compound

HRID 275296Notes

Reaction equation

HRID 275296 reaction equation
[O:1]=[C:2]([CH2:9][CH3:10])[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[CH2:11](O)[CH2:12][OH:13]>C1(C)C=CC=CC=1>[CH2:9]([C:2]1([CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])[O:13][CH2:12][CH2:11][O:1]1)[CH3:10]

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 546293Methyl 4-oxohexanoate

Product 1

HCID 20087711HCID 20087711, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirring solution of 4.05 g (28 mmol) of methyl 4-oxohexanoate (16), prepared as described above in Example 16, in 200 mL of toluene and 0.53 g (2.8 mmol) of tosyl acid was added 5.59 g (90 mmol) of ethylene glycol. After refluxing for 2 hours using a Dean-Stark trap, the solvent was removed under vacuum. The resulting orange oil was dissolved in 200 mL of EtOAc. The EtOAc was then washed with 2×200 mL of H2O. The organic layer was then dried over Na2SO4 anhydrous, filtered, and concentrated in vacuo to yield 4.96 g (94%) of methyl 2-ethyl-1,3-dioxolane-2-propanoate (17), which was employed immediately in Example 18 below.

Workup

  1. temperatureAfter refluxing for 2 hours
  2. customthe solvent was removed under vacuum
  3. dissolutionThe resulting orange oil was dissolved in 200 mL of EtOAc
  4. washThe EtOAc was then washed with 2×200 mL of H2O
  5. dry with materialThe organic layer was then dried over Na2SO4 anhydrous
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cdc32c5468a746e98b49463dcf2be6d0
Source dataset
uspto-grants-1995_02
Patent number
US05393747

Reaction notes

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