Acetic Acid → HCID 131722517, compound

HRID 324425Notes

Reaction equation

HRID 324425 reaction equation
O[N:2]=[C:3]([C:9](=[O:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5].O.[C:21](O)(=[O:23])[CH3:22]>C(OC(=O)C)(=O)C.[Zn]>[C:21]([NH:2][CH:3]([C:9](=[O:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])(=[O:23])[CH3:22]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 178472910HCID 178472910, compound

Product 1

HCID 131722517HCID 131722517, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

Zinc dust (10 micron, 150 g) was added portionwise to a stirred solution of the product from step (i) (88 g) in acetic acid (400 ml) and acetic anhydride (125 ml) keeping the internal temperature below 40° C. The solution was stirred at room temperature for a further 1 hour before adding water (500 ml) dropwise at such a rate so as to keep the internal temperature below 40° C. The mixture was stirred at room temperature for a further 16 h then filtered and the mother liquor extracted with chloroform. The organic extracts were further washed with brine and water, collected dried over magnesium sulphate and solvent removed under reduced pressure to give the subtitle product.

Workup

  1. customthe internal temperature below 40° C
  2. customthe internal temperature below 40° C
  3. stirringThe mixture was stirred at room temperature for a further 16 h
  4. filtrationthen filtered
  5. extractionthe mother liquor extracted with chloroform
  6. washThe organic extracts were further washed with brine and water
  7. customcollected
  8. dry with materialdried over magnesium sulphate and solvent
  9. customremoved under reduced pressure

Sources & evidence

ORD record
ord-47efe3e81ebb4afdbb546a408f16978d
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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