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

HRID 128906노트

반응식

HRID 128906 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fff4608bab8e48bda897c2cbb38ab6d5
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466661

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