2-Methyl-3-phenylprop-2-enoic acid → Benzoic Acid

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.

1. additionwas added in one portion
2. stirringThe reaction was stirred at room temperature for 3 hours or until the solution
3. customthe completion of the reaction which
4. stirringstirred for an additional hour or until solution
5. extractionto extract the products and 1N HCl
6. dissolutionto dissolve the salts
7. extractionThe organic extract
8. washwas washed with 1N HCl (30 mL×3) and brine (30 mL)
9. dry with materialdried over Na2SO4
10. customthe solvent was removed under reduced pressure
11. customto obtain the crude product

ORD record

ord-91caa776d8d14826ad35879e3ec82cf6

Source dataset

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06787671B2