Ethylene Glycol → 2-((Benzyloxy)methyl)-2-methyl-1,3-dioxolane

HRID 1645634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1645634
[CH2:1]([O:8][CH2:9][C:10](=[O:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:13](O)[CH2:14][OH:15].C(OCC)(OCC)OCC>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>[CH2:1]([O:8][CH2:9][C:10]1([CH3:11])[O:15][CH2:14][CH2:13][O:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 174Ethylene GlycolHCID 31214Ethyl orthoformateHCID 36912841-(Benzyloxy)propan-2-one

Produkt 1

HCID 597925942-((Benzyloxy)methyl)-2-methyl-1,3-dioxolaneAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A mixture of 1-benzyloxy-2-propanone (4.94 g, 30.1 mmol), ethylene glycol (20 ml, 359 mmol), triethyl orthoformate (5 ml, 30.1 mmol), and p-toluenesulfonic acid monohydrate (130 mg, 0.683 mmol) was stirred at room temperature for 61.5 hours. To the reaction mixture, a saturated aqueous sodium hydrogen carbonate solution (20 ml) was added and the mixture was extracted twice with chloroform (50 ml) and the organic layer was dried over anhydrous sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 4/1 gradient). Desired fractions were concentrated to obtain the title compound (5.67 g, 90.5% yield) as a colorless oil.

Aufarbeitung

  1. extractionthe mixture was extracted twice with chloroform (50 ml)
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 4/1 gradient)
  5. concentrationDesired fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-be08dc1ac0964e0ab2af1a7000be2d3c
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124780B2

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