Hydrochloric Acid → 3-Phenyl-5-butyrylisoxazole

HRID 1613871

Reaction equation

HRID 1613871 reaction equation
[OH:1][CH:2]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=1)[CH2:3][CH2:4][CH3:5].Cl[O-].[Na+].N1C=CC=CC=1.Cl>ClCCl>[C:2]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=1)(=[O:1])[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 108893475-(1-Hydroxybutyl)-3-phenylisoxazoleHCID 23665760Sodium Hypochlorite

Product 1

HCID 101306023-Phenyl-5-butyrylisoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

In 12.5 ml of dichloromethane, 4.4 g (20 mmol) of 5-(1-hydroxybutyl)-3-phenylisoxazole were dissolved. While the solution was being stirred, 35.2 g (60 mmol) of a 12.7% aqueous solution of sodium hypochlorite were added dropwise to the solution. Next, a liquid mixture which had been obtained by adding 0.48 g (6.1 mmol) of pyridine to 1.0 ml of 6 N hydrochloric acid) was added dropwise over 1 hour and the reaction temperature was maintained at 20° C. After completion of the reaction, the organic layer was collected and was washed successively with a 5% aqueous solution of sodium hydrogensulfite, water and 1 N hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was then recrystallized from ethanol, whereby the target compound, namely, 5-butyryl-3-phenylisoxazole was obtained as crystals.

Workup

  1. customNext, a liquid mixture which had been obtained
  2. additionwas added dropwise over 1 hour
  3. customAfter completion of the reaction
  4. customthe organic layer was collected
  5. washwas washed successively with a 5% aqueous solution of sodium hydrogensulfite, water and 1 N hydrochloric acid
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was then recrystallized from ethanol, whereby the target compound

Sources & evidence

ORD record
ord-1908d19f4e824681a929efddc870ea34
Source dataset
uspto-grants-1993_03
Patent number
US05194606

Linked notes

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