Hydrochloric Acid → 5-(4-Hydroxyphenyl)isoxazol-3-ol

HRID 612960Notes

Reaction equation

HRID 612960 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13]C)=[CH:9][CH:8]=2)[O:4][N:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCl>[OH:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[O:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 178488712HCID 178488712, compound

Product 1

HCID 1785158765-(4-Hydroxyphenyl)isoxazol-3-olYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Hydroxy-5-(4-methoxyphenyl)isoxazole (5.0 g) was suspended in dichloromethane (50 ml), and aluminum chloride (7.0 g) was added thereto, followed by reflux of the resulting mixture for 66 hours. At the end of this time, the reaction mixture was poured into ice-cold water, and 6N hydrochloric acid was added thereto, followed by extraction with ethyl acetate. After the extract was washed with a saturated aqueous NaCl solution, the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: cyclohexane/ethyl acetate=2/1) to obtain the title compound (3.8 g, 83%) as colorless crystals.

Workup

  1. temperatureby reflux of the resulting mixture for 66 hours
  2. additionwas added
  3. extractionfollowed by extraction with ethyl acetate
  4. washAfter the extract was washed with a saturated aqueous NaCl solution
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: cyclohexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-07962bb1fb604bfc82e16da201168c31
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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