Anisole → HCID 136133815, compound

HRID 279467Notes

Reaction equation

HRID 279467 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][N:7]=[C:8]([C:25]1[N:29]=[C:28]([CH3:30])[O:27][N:26]=1)[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[O:16]CC1C=CC(Cl)=CC=1.C1(OC)C=CC=CC=1>C(=O)(O)[O-].[Na+]>[CH3:5][O:6][N:7]=[C:8]([C:25]1[N:29]=[C:28]([CH3:30])[O:27][N:26]=1)[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[OH:16]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 53672687HCID 53672687, compound

Product 1

HCID 136133815HCID 136133815, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Aluminium chloride (0.27 g, 2 mmol) was added to a mixture of 5-chloro-2-(4-chlorobenzyloxy)phenyl 5-methyl-1,2,4-oxadiazol-3-yl ketone O-methyloxime (0.39 g, 1 mmol) and anisole (3 ml) under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, aqueous sodium bicarbonate solution (100 ml) was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 5-chloro-2-hydroxyphenyl 5-methyl-1,2,4-oxadiazol-3-yl ketone O-methyloxime (0.22 g, 82.2%) as colorless crystals. A part of the crystals was recrystallized from ether/n-hexane to give crystals (mp. 92-93.5° C.)

Workup

  1. temperaturecooling
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-5292c29e99804939864d3e2b207377f5
Source dataset
uspto-grants-2002_03
Patent number
US06362212B1

Reaction notes

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