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

HRID 31574

Reaktionsgleichung

Reaktionsgleichung von HRID 31574
[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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-768326b17c3f4dd5bb13a20fb6733919
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425634B2

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