Sulfuric Acid → HCID 178467588, compound

HRID 465443Notes

Reaction equation

HRID 465443 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11](Br)[CH:12](Br)[C:13]([O:15]C)=O)=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].Cl.[NH2:20][OH:21].[OH-].[K+].S(=O)(=O)(O)O>CO.O>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:21][N:20]=[C:13]([OH:15])[CH:12]=2)=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 19874520HCID 19874520, compound

Product 1

HCID 178467588HCID 178467588, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of methyl 3-(4-acetonylphenyl)-2,3-dibromopropionate, ethylene ketal (4.2 g) in methanol (25 ml) was added dropwise to a stirred mixture of hydroxylamine hydrochloride (0.86 g) and potassium hydroxide (3.9 g) in methanol: water (150 ml) at ambient temperature and stirred for 1 h. The reaction mixture was then heated under reflux for 7 h, cooled, acidified with sulphuric acid (50%), filtered, and the solvent removed under reduced pressure. The residue was partitioned between ethylacetate and water, dried (magnesium sulphate), filtered and evaporated to dryness in vacuo. The residue was purified by column chromatography on silica using chloroform as eluent, and crystallised from diethylether-(60°-80°)petroleum ether to give 5-(4-acetonylphenyl)-3-hydroxyisoxazole (0.5 g).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureunder reflux for 7 h
  3. temperaturecooled
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe residue was partitioned between ethylacetate and water
  7. dry with materialdried (magnesium sulphate)
  8. filtrationfiltered
  9. customevaporated to dryness in vacuo
  10. customThe residue was purified by column chromatography on silica
  11. customcrystallised from diethylether-(60°-80°)petroleum ether

Sources & evidence

ORD record
ord-bea19741acc54224b49848322adea0bc
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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