9-Decen-1-ol → 2-Propenoic acid, 3-(2-hydroxyphenyl)-, 9-decen-1-yl ester, (2E)-

HRID 655070

Reaktionsgleichung

Reaktionsgleichung von HRID 655070
[CH2:1]([O:3][C:4](=[O:14])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13])[CH3:2].[CH2:15](O)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]C=C>CCOCC>[CH2:1]([O:3][C:4](=[O:14])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13])[CH2:2][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=[CH2:15]

Komponenten

4

Edukt 2

HCID 256129-Decen-1-olHCID 576496Ethyl 3-(2-hydroxyphenyl)prop-2-enoate

Produkt 1

HCID 177820092-Propenoic acid, 3-(2-hydroxyphenyl)-, 9-decen-1-yl ester, (2E)-Ausbeute 21,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 5.0 g 3-(2-hydroxy-phenyl)-acrylic acid ethyl ester, 6.1 g dec-9-en-1-ol and 1.0 g tetraisopropyl-ortho-titanate was heated to 150° C. removing the ethanol formed. After stirring for 2.5 hours at this temperature, the reaction mixture was cooled, diluted with ether and washed with brine. The organic phase was dried and evaporated to dryness. The resulting oil was Kugelrohr-distilled, crystallized and recrystallized to yield 1.69 g of colourless crystals.

Aufarbeitung

  1. customremoving the ethanol
  2. customformed
  3. temperaturethe reaction mixture was cooled
  4. washwashed with brine
  5. customThe organic phase was dried
  6. customevaporated to dryness
  7. distillationThe resulting oil was Kugelrohr-distilled
  8. customcrystallized
  9. customrecrystallized

Quellen und Nachweise

ORD-Eintrag
ord-ff72df1e00034eddb3180f5fcfb72700
Quelldatensatz
uspto-grants-2011_12
Patentnummer
USRE043006E1

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