Anisole → 2-hydroxy-alpha-(1-imidazolyl)benzaldehyde O-methyloxime

HRID 1489385Notes

Reaction equation

HRID 1489385 reaction equation
C1(OC)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:13][O:14][N:15]=[C:16]([N:33]1[CH:37]=[CH:36][N:35]=[CH:34]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23]CC1C=CC(Cl)=CC=1Cl>C(=O)(O)[O-].[Na+]>[CH3:13][O:14][N:15]=[C:16]([N:33]1[CH:37]=[CH:36][N:35]=[CH:34]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 542129432-(2,4-dichlorobenzyloxy)-alpha-(1-imidazolyl)benzaldehyde O-methyloxime

Product 1

HCID 1359761652-hydroxy-alpha-(1-imidazolyl)benzaldehyde O-methyloximeYield 78.5%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Dry anisole (6 ml) and aluminium chloride (0.59 g) were added to 2-(2,4-dichlorobenzyloxy)-α-(1-imidazolyl)benzaldehyde O-methyloxime (0.75 g), and the mixture was stirred under ice-cooling for 2 hours. After completion of the reaction, a half-saturated aqueous solution of sodium bicarbonate (100 ml) was added slowly, and the mixture was extracted with ether (50 ml) and ethyl acetate (50 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography and recrystallized from ethyl acetate/n-hexane to give 2-hydroxy-α-(1-imidazolyl)benzaldehyde O-methyloxime (0.34 g) as colorless crystals. mp. 103.5°-104.5° C.

Workup

  1. temperaturecooling for 2 hours
  2. customAfter completion of the reaction
  3. extractionthe mixture was extracted with ether (50 ml) and ethyl acetate (50 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude product was purified by silica gel chromatography
  7. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-c4cfeef94b1d4e55a1df45554774277c
Source dataset
uspto-grants-1997_10
Patent number
US05677465

Reaction notes

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