Dimethyl Sulfoxide → Benzenemethanol, alpha-ethenyl-, 1-acetate

HRID 1983976

Reaktionsgleichung

Reaktionsgleichung von HRID 1983976
[CH:1]([CH:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:2].[C:11]([O-:14])(=[O:13])[CH3:12].[K+].CS(C)=O>O>[C:11]([O:14][CH:3]([CH:1]=[CH2:2])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:13])[CH3:12]

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 517044Potassium AcetateHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-

Produkt 1

HCID 111277Benzenemethanol, alpha-ethenyl-, 1-acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

In a one liter 3-neck round bottom flask equipped with a condenser, mechanical stirrer and thermometer, 108 grams (0.708 mol) of vinylbenzyl chloride (60/40 m-/p-) and 808 grams (0.815 mol) of potassium acetate were added, followed by 250 mLs of DMSO. The mixture was stirred at 40° C. for 48 hours. After allowing to cool to room temperature, the mixture was diluted with water and poured into a separatory funnel. The organic layer was separated, followed by an extraction of the aqueous layer with chloroform. The combined organic layer was then washed with water, dried over magnesium sulfate and placed on the rotary evaporator to remove the chloroform. 120 grams of the vinylbenzyl acetate product was recovered, to which 10 mg of MEHQ was added as an inhibitor.

Aufarbeitung

  1. customIn a one liter 3-neck round bottom flask equipped with a condenser, mechanical stirrer
  2. temperatureto cool to room temperature
  3. additionpoured into a separatory funnel
  4. customThe organic layer was separated
  5. extractionfollowed by an extraction of the aqueous layer with chloroform
  6. washThe combined organic layer was then washed with water
  7. dry with materialdried over magnesium sulfate
  8. customplaced on the rotary evaporator
  9. customto remove the chloroform
  10. custom120 grams of the vinylbenzyl acetate product was recovered, to which 10 mg of MEHQ
  11. additionwas added as an inhibitor

Quellen und Nachweise

ORD-Eintrag
ord-af0c0b19934242bfaa47c6791779d4f5
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544453B2

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