Sulfuric Acid → HCID 13537601, compound

HRID 638554Notes

Reaction equation

HRID 638554 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([C:9]2[CH:13]=[C:12]([CH2:14][CH2:15][OH:16])[O:11][N:10]=2)=[O:8])=[CH:5][CH:4]=1.[OH:19]S(O)(=O)=O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([C:9]2[CH:13]=[C:12]([CH2:14][C:15]([OH:19])=[O:16])[O:11][N:10]=2)=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 13809955HCID 13809955, compound

Product 1

HCID 13537601HCID 13537601, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 24.7 g of 2-[3-(4-methoxybenzoyl)-isoxazol-5-yl]ethanol and a few crystals of tetrabutylammonium hydrogen sulfate in 2 liter of CH2Cl2 was added 300 ml of 9M H2SO4. To this was added 29.4 g of pulverized K2Cr2O7 and the mixture was stirred at room temperature for 15 minutes. The organic phase was separated from the aqueous phase and washed with water. The acid product was extracted from the organic phase using 300 ml of 3% NaHCO3. The alkaline solution was washed with CH2Cl2 several times, 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 give 2.6 g of a powder. Recrystallization from 50 ml of toluene yielded 2.3 g (9%) of needles, m.p. 119°-121°.

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
  5. customprecipitated
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-b6c8ddf352044431824e01a687de8076
Source dataset
uspto-grants-1985_12
Patent number
US04562187

Reaction notes

Loading…