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

HRID 1489385ノート

反応式

HRID 1489385 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c4cfeef94b1d4e55a1df45554774277c
出典データセット
uspto-grants-1997_10
特許番号
US05677465

反応ノート

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