Water → HCID 178423844, compound

HRID 506433Notes

Reaction equation

HRID 506433 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]([O:12]C)=[O:11])=[CH:4][CH:3]=1.Cl.[NH2:16]O.[OH-].[Na+].O>CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([OH:12])[O:11][N:16]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 291780methyl 3-(4-methylphenyl)-3-oxopropanoateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 178423844HCID 178423844, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to method of U.S. Pat. No. 3,781,438, 2 g of methyl 3-(4-methylphenyl)-3-oxopropanoate was dissolved in methanol, slightly excessive hydroxylamine hydrochloride and equivalent amount of sodium hydroxide were added, the mixture was heated to reflux. 3 hr later, the reaction was traced by Thin-Layer Chromatography, after the reaction, water was added to the reaction mixture, extracted with ethyl acetate, The combined organic extracts were dried and concentrated to obtain 3-(4-methylphenyl)isoxazol-5-ol as solid (compound III-3).

Workup

  1. temperaturethe mixture was heated to reflux
  2. custom3 hr
  3. additionwas added to the reaction mixture
  4. extractionextracted with ethyl acetate
  5. customThe combined organic extracts were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6372c26c00e94c609b4d3a29f03f5a7b
Source dataset
uspto-grants-2010_08
Patent number
US07786045B2

Reaction notes

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