Acetic Acid → HCID 14324462, compound

HRID 1460816Notes

Reaction equation

HRID 1460816 reaction equation
C[C:2]1O[N:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=2[N+:17]([O-:19])=[O:18])[C:4](=[O:20])[CH:3]=1.C=O.S(=O)(=O)(O)O.[ClH:28].[C:29]([OH:32])(=O)[CH3:30]>[Cl-].[Zn+2].[Cl-]>[Cl:28][CH2:2][C:3]1[C:4](=[O:20])[N:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=2[N+:17]([O-:19])=[O:18])[O:32][C:29]=1[CH3:30]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 14324454HCID 14324454, compound

Product 1

HCID 14324462HCID 14324462, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

After mixing 165 g (0.573) of 5-methyl-2-(4-trifluoromethyl-2-nitrophenyl)-4-isoxazolin-3-one prepared in the above step, 156.2 g of zinc chloride, 206.3 g of paraformaldehyde, and 5 ml of sulfuric acid, 400 ml of acetic acid was added to the mixture followed by stirring. The reaction system was saturated with hydrogen chloride gas at room temperature and the mixture was refluxed for 8 hours while blowing hydrogen chloride gas into the system. Thereafter, the reaction mixture was cooled and poured into ice-water and the product formed was extracted with ethyl acetate. Then, after removing colored components by a short column of silica gel, the product was recrystallized from a 4:1 mixture of n-hexane and ethyl acetate to provide 110 g of the desired product with a yield of 57%. The melting point thereof was 68° C. to 70° C.

Workup

  1. additionwas added to the mixture
  2. temperaturethe mixture was refluxed for 8 hours
  3. temperatureThereafter, the reaction mixture was cooled
  4. customthe product formed
  5. extractionwas extracted with ethyl acetate
  6. customThen, after removing colored components by a short column of silica gel
  7. customthe product was recrystallized from a 4:1 mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-ef271cba31814e93baa617f220906c3f
Source dataset
uspto-grants-1991_12
Patent number
US05071994

Reaction notes

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