Réaction #2075686

Équation de réaction

3,4-Dihydroxybenzaldehyde

Cesium carbonate

Oleyl mesylate

→

yellow oil

Rendement 89.2%

Dioleyloxybenzaldehyde

Rendement 89.2%

Solvants

diglyme

Conditions de réaction

Traitement

1. 1
   Autresealed
2. 2
   Autreflushed with argon
3. 3
   TempératureThe reaction mixture was cooled to room temperature
4. 4
   Filtrationfiltered
5. 5
   LavageThe solids were washed with 1,2-dichloroethane
6. 6
   ConcentrationThe combined filtrate and washes were concentrated
7. 7
   Autredried under high vacuum at 65° C.
8. 8
   Autreto remove residual diglyme
9. 9
   AutreThe resultant yellow oil was purified via flash chromatography (5% ethyl acetate in hexanes)

Mode opératoire

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.

Source