Reaction #2195478

Reaction equation

3,4-Dihydroxybenzaldehyde

Cesium carbonate

Oleyl mesylate

→

yellow oil

Yield 89.2%

Dioleyloxybenzaldehyde

Yield 89.2%

Solvents

diglyme

Conditions

Workup

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

Procedure

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