Reacción #742252

ord-ff72df1e00034eddb3180f5fcfb72700

Ecuación de reacción

CCOC(=O)C=Cc1ccccc1O
3-(2-hydroxy-phenyl)-acrylic acid ethyl ester
C=CCCCCCCCCO
dec-9-en-1-ol
C=CCCCCCCCCOC(=O)/C=C/c1ccccc1O
colourless crystals
Rendimiento 21.5%
C=CCCCCCCCCOC(=O)/C=C/c1ccccc1O
(E)-3-(2-Hydroxy-phenyl)-acrylic acid dec-9-enyl ester
Rendimiento 21.5%

Disolventes

Condiciones de reacción

Temperatura
150°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroremoving the ethanol
  2. 2
    Otroformed
  3. 3
    Temperaturathe reaction mixture was cooled
  4. 4
    Lavadowashed with brine
  5. 5
    OtroThe organic phase was dried
  6. 6
    Otroevaporated to dryness
  7. 7
    workup.DISTILLATIONThe resulting oil was Kugelrohr-distilled
  8. 8
    Otrocrystallized
  9. 9
    Otrorecrystallized

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: USRE043006E1uspto-grants-2011_12