Sulfuric Acid → HCID 20348777, compound

HRID 1730756Notes

Reaction equation

HRID 1730756 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([S:16]([CH2:18][C:19]([OH:21])=[O:20])=[O:17])[CH3:15])=[CH:10][CH:9]=1.S(=O)(=O)(O)[OH:23].[Mn]([O-])(=O)(=O)=O.[K+]>CC(C)=O.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([S:16]([CH2:18][C:19]([OH:21])=[O:20])(=[O:23])=[O:17])[CH3:15])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 516875Potassium PermanganateHCID 20348737HCID 20348737, compound

Product 1

HCID 20348777HCID 20348777, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

170 gm (0.556 mol) of a diastereoisomeric mixture of [1-(2'-fluoro-4-biphenylyl)-ethylsulfinyl]-acetic acid were dissolved in 1.7 liters of acetone, and a solution of 19.9 gm (0.195 mol) of concentrated sulfuric acid in 70 ml of water was added. While stirring, 67.2 gm (0.425 mol) of potassium permanganate were added in small portions, and the temperature was maintained at 20°-25° C. The mixture was stirred for 1 hour, the manganese dioxide was suction-filtered off, the filter cake was washed with acetone, and the filtrate was evaporated in vacuo. The residue was diluted with 4 liters of glacial acetic acid, and the precipitated crystalline reaction product was suction-filtered off, washed, dried and recrystallized from toluene. Yield: 158.2 gm (88.5% of theory); m.p. 144°-146° C.

Workup

  1. temperaturethe temperature was maintained at 20°-25° C
  2. stirringThe mixture was stirred for 1 hour
  3. filtrationthe manganese dioxide was suction-filtered off
  4. washthe filter cake was washed with acetone
  5. customthe filtrate was evaporated in vacuo
  6. additionThe residue was diluted with 4 liters of glacial acetic acid
  7. filtrationthe precipitated crystalline reaction product was suction-filtered off
  8. washwashed
  9. customdried
  10. customrecrystallized from toluene

Sources & evidence

ORD record
ord-f9d6bd722986432692b339b512db01ba
Source dataset
uspto-grants-1976_11
Patent number
US03993683

Reaction notes

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