Reaktion #58013

Reaktionsgleichung

water

9-decenoxybenzyltriphenylphosphonium bromide

compound ( 26 )

9-decenoxybenzyltriphenylphosphonium bromide

terephthalaldehyde

compound ( 12 )

terephthalaldehyde

sodium ethoxide ethanol

→

9-decenoxystilbene aldehyde

Ausbeute 50.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITat a mixture temperature of 10° C. to 15° C. for 2 hours
2. 2
   FiltrationThen, the precipitated crystals were filtrated
3. 3
   Waschenwashed with 50 mL of 60% aqueous ethanol and 30 mL of ethanol
4. 4
   Sonstigeby drying

Vorschrift

First, 23.07 g (0.039 M) of 9-decenoxybenzyltriphenylphosphonium bromide (compound (26)) prepared in Synthetic example 1-4 and 5.91 g of terephthalaldehyde (compound (12)) were dissolved in 315 mL of ethanol. The resulting solution was cooled to −2° C., and then 25.64 g of a sodium ethoxide ethanol solution (21 percent by weight, aldrich) was added dropwise at 0° C. or less. Aging was performed at a mixture temperature of 0° C. or less for 1.5 hours and then at a mixture temperature of 10° C. to 15° C. for 2 hours. After aging, 39 g of deionized water was added dropwise. Then, the precipitated crystals were filtrated and washed with 50 mL of 60% aqueous ethanol and 30 mL of ethanol, followed by drying. Thereby, 7.12 g of 9-decenoxystilbene aldehyde (compound (27)) was produced (yield: 50.0%).

Quelle