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Ethyl behenate → 1-Phenylethanol, (S)-

HRID 1939748
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1939748
C(OCC)(=O)CCCCCCCCCCCCCCCCCCCCC.C([O:50][CH:51]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[CH3:52])(=O)CCCCCCCCCCCCCCCCCCCCC>O>[C:53]1([C@@H:51]([OH:50])[CH3:52])[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 22199Ethyl behenateHCID 21468167HCID 21468167, Verbindung

Produkt 1

HCID 4431351-Phenylethanol, (S)-Ausbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Interesterification was carried out by using 1 g of Lipase QL, 40 g of (R,S)-1-phenylethanol, and 60 g of ethyl behenate under the same conditions as in Example 6 at 95° C. for a period of 20 hours. The water content of the reaction system was 0.03% by weight, and 95% of the lipase particles had a particle size of 20 to 40 μm. Gas chromatography of the reaction mixture revealed that 47 mol % of (R,S)-1-phenylethanol had been converted to 1-phenylethyl behenate. The reaction mixture was treated in the same manner as in Example 6 and subjected to simple distillation at 85° C. and 5 mmHg to give (S)-(-)-1-phenylethanol (yield: 97%; chemical purity: 99.9%; optical purity: 88.9% ee). On the other hand, the residue, i.e., a mixture of (R)-(+)-1-phenylethyl behenate and unreacted ethyl behenate was alkali-hydrolyzed in the same manner as in Example 1, and 1000 ml of acetone was added to the reaction mixture, followed by cooling to 5° C. The precipitated behenic acid was removed by filtration to obtain (R)-(+)-1-phenylethanol (yield: 88%; chemical purity: 99.9%; optical purity: 98.5% ee).

Aufarbeitung

  1. customat 95° C.
  2. customof 20 hours
  3. additionThe reaction mixture was treated in the same manner as in Example 6
  4. distillationsubjected to simple distillation at 85° C.

Quellen und Nachweise

ORD-Eintrag
ord-598976ab3ae643499fcaaceceb9e4a9a
Quelldatensatz
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05696299

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