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Phosphorus pentachloride → alpha-chloro-2-(2,4-dichlorobenzyloxy)benzaldehyde O-methyloxime

HRID 1489382
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HRID 1489382 반응식
[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[CH2:4][O:5][C:6]1[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=1[C:8]([NH:10][O:11][CH3:12])=O.P(Cl)(Cl)(Cl)(Cl)[Cl:23].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:12][O:11][N:10]=[C:8]([Cl:23])[C:7]1[CH:13]=[CH:14][CH:15]=[CH:16][C:6]=1[O:5][CH2:4][C:3]1[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:2]=1[Cl:1]
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참가 물질

5

반응물 3

HCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 229044802-(2,4-Dichlorobenzyloxy)-N-methoxybenzamide

생성물 1

HCID 53754588alpha-chloro-2-(2,4-dichlorobenzyloxy)benzaldehyde O-methyloxime수율 86.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

2-(2,4-Dichlorobenzyloxy)-N-methoxybenzamide (10.44 g) was dissolved in dry methylene chloride (100 ml), phosphorus pentachloride (6.66 g) was added under ice-cooling over about 3 minutes to the solution, and the mixture was stirred at 0° C. for 1 hour. After completion of the reaction, a saturated aqueous solution of sodium bicarbonate (150 ml) was added slowly, and the mixture was extracted with methylene chloride (150 ml) twice, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography to give α-chloro-2-(2,4-dichlorobenzyloxy)benzaldehyde O-methyloxime (9.52 g) as crystals. A part of the crystals was recrystallized from ethyl acetate/n-hexane to give colorless crystals. mp 91°-92° C.

후처리

  1. temperaturecooling over about 3 minutes to the solution
  2. customAfter completion of the reaction
  3. extractionthe mixture was extracted with methylene chloride (150 ml) twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude product was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-ed0796203af74e27be92845404573fe5
출처 데이터셋
uspto-grants-1997_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05677465

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