تفاعل #1093489

معادلة التفاعل

Na2SO3

OXONE

NaHCO3

α-Methyl cinnamic acid

→

Benzoic acid

المردود 82.0%

المذيبات

EtOAc

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added in one portion
2. 2
   workup.STIRRINGThe reaction was stirred at room temperature for 3 hours or until the solution
3. 3
   أخرىthe completion of the reaction which
4. 4
   workup.STIRRINGstirred for an additional hour or until solution
5. 5
   استخلاصto extract the products and 1N HCl
6. 6
   workup.DISSOLUTIONto dissolve the salts
7. 7
   استخلاصThe organic extract
8. 8
   غسيلwas washed with 1N HCl (30 mL×3) and brine (30 mL)
9. 9
   تجفيفdried over Na2SO4
10. 10
    أخرىthe solvent was removed under reduced pressure
11. 11
    أخرىto obtain the crude product

الإجراء التجريبي

The α-Methyl cinnamic acid (100 mg) was dissolved in DMF (5 mL), and OsO4 (0.076 mL, 2.5% in tBuOH) was added and stirred for 5 min. A solid mixture of OXONE (1.52 g) and NaHCO3 (0.206 g) was added in one portion and the reaction had a final volume (7 mL). The reaction was stirred at room temperature for 3 hours or until the solution becomes colorless. This usually marks the completion of the reaction which was verified by TLC or GC. Na2SO3 (600 mg) was added, to reduce the remaining Os(VIII), and stirred for an additional hour or until solution became dark brown/black. EtOAc was added to extract the products and 1N HCl was used to dissolve the salts. The organic extract was washed with 1N HCl (30 mL×3) and brine (30 mL), dried over Na2SO4, and the solvent was removed under reduced pressure to obtain the crude product. Benzoic acid was obtained in 82% yield, 90% yield by GC, without the need for further purification.

المصدر