Ethylene Glycol → Methyl 2-(2-isopropyl-1,3-dioxolan-2-yl)acetate

HRID 1191747Notes

Reaction equation

HRID 1191747 reaction equation
[CH3:1][CH:2]([CH3:10])[C:3](=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].[CH2:11](O)[CH2:12][OH:13]>C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>[CH:2]([C:3]1([CH2:4][C:5]([O:7][CH3:8])=[O:6])[O:13][CH2:12][CH2:11][O:9]1)([CH3:10])[CH3:1]

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 2759969Methyl 4-methyl-3-oxopentanoate

Product 1

HCID 13085712Methyl 2-(2-isopropyl-1,3-dioxolan-2-yl)acetateYield 71.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

To a solution of methyl 4-methyl-3-oxopentanoate (72 g, 0.5 mol), and ethylene glycol (56 g, 1 mol) in toluene (500 mL) was added 4-methylbenzenesulfonic acid (1.9 g, 0.01 mol). The mixture was stirred at reflux with a Dean-Stark trap to remove water. The reaction mixture was washed with a small amount of water and brine, dried over anhydrous Na2SO4, and concentrated in vacuum to give the crude methyl 2-(2-isopropyl-1,3-dioxolan-2-yl)-acetate (67 g 71% yield), which was used for the next step without further purification.

Workup

  1. temperatureat reflux with a Dean-Stark trap
  2. customto remove water
  3. washThe reaction mixture was washed with a small amount of water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-021561f693c74a29b829eff370eff3cd
Source dataset
uspto-grants-2014_03
Patent number
US08680093B2

Reaction notes

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