Reaktion #2195478

Reaktionsgleichung

3,4-Dihydroxybenzaldehyde

Cesium carbonate

Oleyl mesylate

→

yellow oil

Ausbeute 89.2%

Dioleyloxybenzaldehyde

Ausbeute 89.2%

Lösungsmittel

diglyme

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigesealed
2. 2
   Sonstigeflushed with argon
3. 3
   TemperaturThe reaction mixture was cooled to room temperature
4. 4
   Filtrationfiltered
5. 5
   WaschenThe solids were washed with 1,2-dichloroethane
6. 6
   EinengenThe combined filtrate and washes were concentrated
7. 7
   Sonstigedried under high vacuum at 65° C.
8. 8
   Sonstigeto remove residual diglyme
9. 9
   SonstigeThe resultant yellow oil was purified via flash chromatography (5% ethyl acetate in hexanes)

Vorschrift

3,4-Dihydroxybenzaldehyde (2.76 g, 20.0 mmol) was weighed into a 200 mL round bottomed flask with a stir bar. The flask was charged with diglyme (100 mL), septum sealed and flushed with argon. Cesium carbonate (19.5 g, 60.0 mmol) was added to the solution slowly in portions. Oleyl mesylate (15.2 g, 44.0 mmol) was added via syringe. The reaction mixture was heated to 100° C. under slight positive pressure of argon. The reaction mixture was cooled to room temperature and filtered. The solids were washed with 1,2-dichloroethane. The combined filtrate and washes were concentrated and then dried under high vacuum at 65° C. to remove residual diglyme. The resultant yellow oil was purified via flash chromatography (5% ethyl acetate in hexanes) to afford 11.4 g (89%) of a yellow oil that turned to yellow wax upon standing at room temperature.

Quelle