Sulfuric Acid → HCID 13537602, compound

HRID 638555Notes

Reaction equation

HRID 638555 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH2:12][OH:13])[O:8][N:7]=1)=[O:5].[OH:19]S(O)(=O)=O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[CH:10]=[C:9]([CH2:11][C:12]([OH:19])=[O:13])[O:8][N:7]=1)=[O:5]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 13537594HCID 13537594, compound

Product 1

HCID 13537602HCID 13537602, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 12.8 g of 2-[3-(2,4-dichlorobenzoyl)-isoxazol-5-yl]ethanol and a few crystals of tetra-n-butylammonium hydrogen sulfate in 1000 ml of CH2Cl2 was added 150 ml of 9M H2SO4. To this was added 13.2 g of pulverized K2Cr2O7 and the mixture was stirred at room temperature for 1 hour. The organic phase was separated from the aqueous phase and washed with water. The acid product was extracted from the organic phase using 40 ml of 4% NaHCO3. The alkaline solution was washed with CH2Cl2 several times, until all the neutral impurities were removed, and the solution was then acidified slowly with 5% HCl until all the acid precipitated. The solid was filtered, washed with water, and dried to yield 3.9 g of a powder. Recrystallization from 100 ml of 50% toluene/hexane gave 3.5 g (26%) of crystals, m.p. 108°-109° .

Workup

  1. customThe organic phase was separated from the aqueous phase
  2. washwashed with water
  3. extractionThe acid product was extracted from the organic phase
  4. washThe alkaline solution was washed with CH2Cl2 several times, until all the neutral impurities
  5. customwere removed
  6. customprecipitated
  7. filtrationThe solid was filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-f97de8a2b52942a6995e0932fc5ea954
Source dataset
uspto-grants-1985_12
Patent number
US04562187

Reaction notes

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