تفاعل #939046

معادلة التفاعل

Isobutyl bromide

ethyl 3-cyano-4-hydroxybenzoate

potassium carbonate

→

desired compound

المردود 33.0%

Ethyl 3-Cyano-4-isobutylbenzoate

المردود 33.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to room temperature
2. 2
   استخلاصThe aqueous mixture was extracted with ethyl acetate (200 mL×2)
3. 3
   غسيلThe ethyl acetate portion was washed successively with water (500 mL×2) and aqueous saturated brine (200 mL)
4. 4
   تجفيفdried over anhydrous sodium sulfate
5. 5
   workup.DISTILLATIONto distill the solvent off
6. 6
   أخرىThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4)
7. 7
   workup.DISSOLUTIONThe resulting crystalline product was dissolved in ethyl acetate (50 mL)
8. 8
   درجة الحرارةunder heating
9. 9
   workup.ADDITIONwas added to the mixture
10. 10
    workup.STIRRINGThe hexane solution was stirred
11. 11
    درجة الحرارةcooled to room temperature
12. 12
    workup.STIRRINGfurther stirred for 10 min.
13. 13
    درجة الحرارةunder cooling with ice
14. 14
    ترشيحThe precipitated crystalline product was collected by filtration
15. 15
    غسيلwashed successively with ethyl acetate/hexane (1/5, 60 mL) mixture and hexane (500 mL)
16. 16
    أخرىdried in air

الإجراء التجريبي

Isobutyl bromide (56.1 mL, 512 mmol) was added to a suspension of the ethyl 3-cyano-4-hydroxybenzoate crude product (51.4 g) and potassium carbonate (70.8 g, 512 mmol) in dry DMF (200 mL), stirred at 100° C. for 10 hours, and cooled to room temperature. Ice-water (500 mL) was then added to the cooled suspension. The aqueous mixture was extracted with ethyl acetate (200 mL×2). The ethyl acetate portion was washed successively with water (500 mL×2) and aqueous saturated brine (200 mL), dried over anhydrous sodium sulfate, and placed under reduced pressure to distill the solvent off. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4). The resulting crystalline product was dissolved in ethyl acetate (50 mL) under heating. The mixture was kept hot, while hexane (100 mL) was added to the mixture. The hexane solution was stirred and cooled to room temperature, and further stirred for 10 min. under cooling with ice. The precipitated crystalline product was collected by filtration, washed successively with ethyl acetate/hexane (1/5, 60 mL) mixture and hexane (500 mL), and dried in air, to give 20.8 g (yield 33%) of the desired compound in the form of a pale yellow crystalline product.

المصدر