Acetone → HCID 12392114, compound

HRID 1763538Notes

Reaction equation

HRID 1763538 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=3[CH2:14][OH:15])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)=[O:22].S(=O)(=O)(O)O>O.[O-2].[O-2].[O-2].[Cr+6]>[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=3[C:14]([OH:22])=[O:15])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 54167400HCID 54167400, compound

Product 1

HCID 12392114HCID 12392114, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent

Procedure

A mixture of 6.3 g. (0.025 mole) o-(5-phenyl-3-isoxazolyl)benzyl alcohol in 125 ml. acetone is added dropwise at room temperature to 50 ml. (0.1 mole) of a reagent prepared by dissolving 100 g. (1.0 mole) chromium trioxide in 160 g. of concentrated sulfuric acid and diluting with water to form a 500 ml. solution. The mixture is stirred for 3 hours at room temperature and then filtered. The acetone is evaporated in vacuo and the residue partitioned between ether and water. The resulting layers are separated and the ether washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The resulting solid is triturated with cold ether and filtered to give o-(5-phenyl-3-isoxazolyl) benzoic acid; m.p. 144.5° to 146.5° C.

Workup

  1. additionA mixture of 6.3 g
  2. dissolutionby dissolving 100 g
  3. customto form a 500 ml
  4. filtrationfiltered
  5. customThe acetone is evaporated in vacuo
  6. customthe residue partitioned between ether and water
  7. customThe resulting layers are separated
  8. washthe ether washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. customThe resulting solid is triturated with cold ether
  13. filtrationfiltered

Sources & evidence

ORD record
ord-095969f66bd847c98f6f46fadba3c62d
Source dataset
uspto-grants-1978_09
Patent number
US04112108

Reaction notes

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