Sulfuric Acid → 1-Phenyl-1,2-ethanediol

HRID 347616

Reaktionsgleichung

Reaktionsgleichung von HRID 347616
[OH:1]S(O)(=O)=O.[CH2:6]1[O:14][CH:7]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>[C:8]1([CH:7]([OH:1])[CH2:6][OH:14])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

5

Edukt 2

HCID 1118Sulfuric AcidHCID 7276Styrene Oxide

Produkt 1

HCID 71491-Phenyl-1,2-ethanediolAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A 2 l stirrer fitted with reflux condenser, thermometer and dropping funnel was charged with 600 g of 0.1% strength H2SO4 and 2 g of tetrabutylammonium hydrogensulfate, and then, at 20° C. to 25° C., 200 g (1.67 mol) of styrene oxide (2) were added over the course of 1 h. When the dropwise addition was complete, the mixture was then stirred for 2 h and then worked up. 200 ml of diethyl ether were added to the reaction mixture, and the organic phase was washed until neutral with sodium carbonate solution and water, and dried over Na2SO4, and the solvent was distilled off under reduced pressure, leaving 223 g of crude product (91% pure according to GC).

Aufarbeitung

  1. customA 2 l stirrer fitted
  2. temperaturewith reflux condenser
  3. additionWhen the dropwise addition
  4. washthe organic phase was washed until neutral with sodium carbonate solution and water
  5. dry with materialdried over Na2SO4
  6. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1707c85e4342412397a83f9aa5f4967d
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176176B2

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