Potassium Hydroxide → 3-Methyl-1,2-benzisoxazol-6-ol

HRID 1993719Notes

Reaction equation

HRID 1993719 reaction equation
O[C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[N:11][OH:12])[CH3:10].[OH-].[K+]>CO.O>[CH3:10][C:9]1[C:3]2[CH:4]=[CH:5][C:6]([OH:8])=[CH:7][C:2]=2[O:12][N:11]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 3451682',4'-Dihydroxyacetophenone oxime

Product 1

HCID 1354978903-Methyl-1,2-benzisoxazol-6-olYield 22%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

1.98 g of 1-(2,4-dihydroxyphenyl)ethanone oxime (12 mM) and 1 g of potassium hydroxide (18 mM) are refluxed for 4 days in a methanol/water mixture (100 ml/100 ml). The reaction medium is subsequently concentrated under reduced pressure, acidified to pH=1 with 1N HCl, and then extracted with ethyl acetate. The organic phase obtained is dried over magnesium sulfate and concentrated under reduced pressure. The evaporation residue is purified by silica gel chromatography (methylcyclohexane/ethyl acetate gradient of 70/30 to 30/70; v/v). The expected product is obtained in the form of a white solid (0.39 g) with a yield of 22%.

Workup

  1. concentrationThe reaction medium is subsequently concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. customThe organic phase obtained
  4. dry with materialis dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe evaporation residue is purified by silica gel chromatography (methylcyclohexane/ethyl acetate gradient of 70/30 to 30/70; v/v)

Sources & evidence

ORD record
ord-5c52bc921cce45b9897bc370704681a8
Source dataset
uspto-grants-2010_01
Patent number
US07652032B2

Reaction notes

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