تفاعل #2075686

معادلة التفاعل

3,4-Dihydroxybenzaldehyde

Cesium carbonate

Oleyl mesylate

→

yellow oil

المردود 89.2%

Dioleyloxybenzaldehyde

المردود 89.2%

المذيبات

diglyme

ظروف التفاعل

المعالجة

1. 1
   أخرىsealed
2. 2
   أخرىflushed with argon
3. 3
   درجة الحرارةThe reaction mixture was cooled to room temperature
4. 4
   ترشيحfiltered
5. 5
   غسيلThe solids were washed with 1,2-dichloroethane
6. 6
   تركيزThe combined filtrate and washes were concentrated
7. 7
   أخرىdried under high vacuum at 65° C.
8. 8
   أخرىto remove residual diglyme
9. 9
   أخرىThe resultant yellow oil was purified via flash chromatography (5% ethyl acetate in hexanes)

الإجراء التجريبي

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.

المصدر