Sulfuric Acid → HCID 13537598, compound

HRID 638551Notes

Reaction equation

HRID 638551 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:12]=[C:11]([CH2:13][CH2:14][OH:15])[O:10][N:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH:18]S(O)(=O)=O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[F:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:12]=[C:11]([CH2:13][C:14]([OH:18])=[O:15])[O:10][N:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 13537592HCID 13537592, compound

Product 1

HCID 13537598HCID 13537598, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 13.5 g of 2-[3-(4-fluorobenzoyl)-isoxazol-5-yl]ethanol and a few crystals of tetrabutylammonium hydrogen sulfate in 1 liter of CH2Cl2 was added 150 ml of 9M H2SO4. To this was added 16.9 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 100 ml of 5% NaHCO3. The alkaline solution was washed with CH2Cl2 several times, until all of the neutral impurities were removed, and then acidified slowly with 5% HCl. The precipitated solid was collected, washed with water and dried to yield 6.7 g of a powder. Recrystallization from 180 ml of 50% toluene/hexane gave 5.9 g (41%) of crystals, m.p. 113°-115°.

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. customuntil all of the neutral impurities were removed
  6. customThe precipitated solid was collected
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-71c14408547640d489a7c87cb6a0497f
Source dataset
uspto-grants-1985_12
Patent number
US04562187

Reaction notes

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