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

HRID 31574

Reaction equation

HRID 31574 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>[CH2:7]([O:6][C:4](=[O:5])[CH2:3][C:2]1([CH2:9][CH2:10][CH3:11])[O:14][CH2:13][CH2:12][O:1]1)[CH3:8]

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 press-re 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 press-re

Sources & evidence

ORD record
ord-768326b17c3f4dd5bb13a20fb6733919
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Linked notes

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