Ethylene Glycol → Ethyl (2-propyl-1,3-dioxolan-2-yl)acetate

HRID 1645513Notes

Reaction equation

HRID 1645513 reaction equation
[O:1]=[C:2]([CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:12](O)[CH2:13][OH:14].C(OCC)(OCC)OCC>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[CH2:9]([C:2]1([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[O:14][CH2:13][CH2:12][O:1]1)[CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 31214Ethyl orthoformateHCID 238498Ethyl 3-oxohexanoate

Product 1

HCID 14505110Ethyl (2-propyl-1,3-dioxolan-2-yl)acetateYield 97%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 962WaterSolvent

Procedure

A mixture of ethyl 3-oxohexanoate (5 g, 31.6 mmol), ethylene glycol (3.92 g, 63.2 mmol) and triethyl orthoformate (4.68 g, 31.6 mmol), and p-toluenesulfonic acid monohydrate (544 mg, 2.86 mmol) was stirred at room temperature for 29 hours and 10 minutes. To the reaction mixture, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (6.2 g, 97%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated saline solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-66c789107f1147008e7010f44ee26fa4
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

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