Sulfuric Acid → HCID 13537600, compound

HRID 638553Notes

Reaction equation

HRID 638553 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([C:7]([C:9]2[CH:13]=[C:12]([CH2:14][CH2:15][OH:16])[O:11][N:10]=2)=[O:8])=[CH:3][CH:2]=1.[OH:18]S(O)(=O)=O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[C:1]1([CH3:17])[CH:2]=[CH:3][C:4]([C:7]([C:9]2[CH:13]=[C:12]([CH2:14][C:15]([OH:18])=[O:16])[O:11][N:10]=2)=[O:8])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 13809954HCID 13809954, compound

Product 1

HCID 13537600HCID 13537600, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 10.7 g of 2-[3-(4-toluoyl)isoxazol-5-yl]ethanol, 1000 ml of CH2Cl2, a few crystals of tetra-n-butylammonium hydrogen sulfate and 150 ml of 9M H2SO4 was added 13.6 g of pulverized K2Cr2O7. The resulting mixture was stirred at room temperature for 1.5 hour. After allowing the mixture to settle, it was decanted from the unreacted dichromate. The aqueous phase was extracted with CH2Cl2, and the organics were washed with water and brine, and dried over MgSO4. Concentration gave 11.0 g of an oil which solidified on standing. Recrystallization from toluene gave 4.8 g (43%) of a solid, m.p. 105°-107°.

Workup

  1. customit was decanted from the unreacted dichromate
  2. extractionThe aqueous phase was extracted with CH2Cl2
  3. washthe organics were washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationConcentration

Sources & evidence

ORD record
ord-ca41aab9b93e42f9833bab16fdacff8e
Source dataset
uspto-grants-1985_12
Patent number
US04562187

Reaction notes

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