Acetic Acid → HCID 21325993, compound

HRID 1701350Notes

Reaction equation

HRID 1701350 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:9]=[C:10](CC#N)[CH:11]=[CH:12][CH:13]=2)=[O:7])=[CH:4][CH:3]=1.O.S(=O)(=O)(O)O.[C:25]([OH:28])(=[O:27])[CH3:26]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[C:12]([CH2:26][C:25]([OH:28])=[O:27])[CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:17][CH:18]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 53835796HCID 53835796, compound

Product 1

HCID 21325993HCID 21325993, compound

Procedure

A mixture of 9.61 g of 3-p-chlorobenzoyl phenyl acetonitrile, 75 cc of water, 75 cc of acetic acid and 75 cc of sulfuric acid was refluxed with stirring for 21/2 hours and then cooled and iced for 1 hour. The mixture was vacuum filtered and the precipitate was empasted with water and taken up in 50 cc of a 10% aqueous sodium carbonate solution. The solution was filtered and the filter was washed with water. The pH of the filtrate was adjusted to 5-6 by addition of acetic acid and after being iced for 30 minutes, the mixture was vacuum filtered. The recovered precipitate was washed with water and dried under reduced pressure. The residue was dissolved in 50 cc of refluxing toluene and the solution was treated with activated carbon and filtered. The filter was washed with boiling toluene. The filtrate was cooled and iced for 1 hour and then vacuum filtered. The recovered precipitate was empasted with iced toluene and dried under reduced pressure to obtain 8.37 g of 3-p-chlorobenzoyl phenyl-acetic acid melting at 148° C.

Workup

  1. temperaturewas refluxed
  2. temperaturecooled
  3. waiticed for 1 hour
  4. filtrationfiltered
  5. filtrationThe solution was filtered
  6. washthe filter was washed with water
  7. additionThe pH of the filtrate was adjusted to 5-6 by addition of acetic acid
  8. waitafter being iced for 30 minutes
  9. filtrationfiltered
  10. washThe recovered precipitate was washed with water
  11. customdried under reduced pressure
  12. dissolutionThe residue was dissolved in 50 cc of refluxing toluene
  13. additionthe solution was treated with activated carbon
  14. filtrationfiltered
  15. washThe filter was washed with boiling toluene
  16. temperatureThe filtrate was cooled
  17. waiticed for 1 hour
  18. filtrationvacuum filtered
  19. customdried under reduced pressure

Sources & evidence

ORD record
ord-55ec496af97449e596e7c19d7617e700
Source dataset
uspto-grants-1980_03
Patent number
US04192890

Reaction notes

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