Sulfuric Acid → 2-[3-(4-Chlorobenzoyl)isoxazol-5-yl]propionic acid

HRID 638556Notes

Reaction equation

HRID 638556 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:12]=[C:11]([CH:13]([CH3:16])[CH2:14][OH:15])[O:10][N:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH:19]S(O)(=O)=O>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:12]=[C:11]([CH:13]([CH3:16])[C:14]([OH:19])=[O:15])[O:10][N:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 135375952-[3-(4-Chlorobenzoyl)-isoxazol-5-yl]propan-1-ol

Product 1

HCID 135376032-[3-(4-Chlorobenzoyl)isoxazol-5-yl]propionic acid

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 11.0 g of 2-[3-(4-chlorobenzoyl)-isoxazol-5-yl]propan-1-ol in 1000 ml of CH2Cl2, a few crystals of tetra-n-butylammonium hydrogen sulfate and 150 ml of 9M H2SO4 was added 12.3 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 separated and the organics were washed with water and brine, and dried over MgSO4. Concentration of the product gave 8.0 g of a solid. Recrystallization from toluene with norite for decolorizing gave 2.0 g of a solid, m.p. 119°-123°. A second recrystallization from toluene gave 1.6 g (13%) of a solid, m.p. 122.5°-124.5°.

Workup

  1. customit was decanted from the unreacted dichromate
  2. customThe aqueous phase was separated
  3. washthe organics were washed with water and brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-6e3a568fd2f04a5bb338565dbdde3e56
Source dataset
uspto-grants-1985_12
Patent number
US04562187

Reaction notes

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