Acetic Acid → Acetophenone

HRID 1076063Notes

Reaction equation

HRID 1076063 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#N.[C:7](O)(=O)C.C([O-])(=O)C.[NH4+].O.[C:17]1(C)[CH:22]=CC=[CH:19][CH:18]=1>>[C:4]([C:3]1[CH:1]=[CH:19][CH:18]=[CH:17][CH:22]=1)(=[O:6])[CH3:7]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 1140TolueneHCID 9740Cyanoacetic acidHCID 517165Ammonium Acetate

Product 1

HCID 7410Acetophenone

Procedure

A mixture of 6-fluoro-2-methyl-4-(4'-methylsulfinylphenyl indanone) (30.2 gm.), cyanoacetic acid (10.5 gm.), acetic acid (6.6 g.) and ammonium acetate (1.7 gm.) in dry toluene (20 ml.) is refluxed with stirring for 24 hours while the water is removed continuously in a Dean-Stark separator. The toluene is concentrated, the residue dissolved in 200 ml. of 4 N potassium hydroxide solution (100 ml. ethanol, 100 ml. water) and refluxed for 12 hours. The aqueous solution is evaporated to remove the ethanol, filtered and then acidified with concentrated HCl solution. The preceipitated 6-fluoro-2- 4-(p-methylsulfinylphenyl)-indenyl-1-acetic acid is collected and dried at 70° C in the vacuum oven.

Workup

  1. temperatureis refluxed
  2. customis removed continuously in a Dean-Stark separator
  3. concentrationThe toluene is concentrated
  4. dissolutionthe residue dissolved in 200 ml
  5. temperatureof 4 N potassium hydroxide solution (100 ml. ethanol, 100 ml. water) and refluxed for 12 hours
  6. customThe aqueous solution is evaporated
  7. customto remove the ethanol
  8. filtrationfiltered
  9. customThe preceipitated 6-fluoro-2- 4-(p-methylsulfinylphenyl)-indenyl-1-acetic acid is collected
  10. customdried at 70° C in the vacuum oven

Sources & evidence

ORD record
ord-4e7a5287490d4e108c14a235ce737b48
Source dataset
uspto-grants-1976_05
Patent number
US03954852

Reaction notes

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