Sulfuric Acid → Benzeneacetic acid, 2,3,4,5,6-pentafluoro-alpha-methyl-

HRID 2249001Notes

Reaction equation

HRID 2249001 reaction equation
[F:1][C:2]1[C:7]([CH:8]([CH3:11])[CH2:9][OH:10])=[C:6]([F:12])[C:5]([F:13])=[C:4]([F:14])[C:3]=1[F:15].S(=O)(=O)(O)[OH:17].[Mn]([O-])(=O)(=O)=O.[K+].S(=O)(O)[O-].[Na+]>CC(C)=O>[F:1][C:2]1[C:7]([CH:8]([CH3:11])[C:9]([OH:17])=[O:10])=[C:6]([F:12])[C:5]([F:13])=[C:4]([F:14])[C:3]=1[F:15]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 516875Potassium PermanganateHCID 14651851(+)-2-(Pentafluorophenyl)-1-propanolHCID 23665763Sodium Bisulfite

Product 1

HCID 5743473Benzeneacetic acid, 2,3,4,5,6-pentafluoro-alpha-methyl-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a vigorously stirred mixture of 9.05 g of (+)-2-(pentafluorophenyl)-1-propanol, 25 ml of acetone and 100 ml of 3N sulfuric acid, was added portionwise 12.6 g of potassium permanganate over six hours. After the mixture was further stirred for 30 minutes, this reaction mixture was poured into 150 ml of an aqueous solution of 15% sodium bisulfite, and extracted with ethyl acetate. The organic layer was extracted with an aqueous solution of 5% potassium carbonate. This aqueous layer was acidified with concentrated hydrochloric acid followed by extraction with ethyl acetate. This extracted solution was then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the subsequent distillation under reduced pressure gave 8.23 g of (-)-2-(pentafluorophenyl)propionic acid having the aforementioned physical properties.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic layer was extracted with an aqueous solution of 5% potassium carbonate
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThis extracted solution was then dried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. distillationthe subsequent distillation under reduced pressure

Sources & evidence

ORD record
ord-ad058aae19594d62a77994902bae0d32
Source dataset
uspto-grants-1991_08
Patent number
US05041641

Reaction notes

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