Methane → 2-(Pyridin-4-ylmethoxy)benzaldehyde

HRID 380182노트

반응식

HRID 380182 반응식
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[OH-].[K+].Cl.[N:13]1[CH:18]=[CH:17][C:16]([CH2:19]Cl)=[CH:15][CH:14]=1.C>CS(C)=O.C(OCC)(=O)C.O>[N:13]1[CH:18]=[CH:17][C:16]([CH2:19][O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[CH:1]=[O:9])=[CH:15][CH:14]=1

참가 물질

8

반응물 4

HCID 297MethaneHCID 6998SalicylaldehydeHCID 14797Potassium HydroxideHCID 745704-(Chloromethyl)pyridinium chloride

생성물 1

HCID 167689982-(Pyridin-4-ylmethoxy)benzaldehyde수율 62.1%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of salicylaldehyde (5 g, 40.9 mmol) in DMSO (75 mL) was treated with crushed potassium hydroxide (5.4 g, 81.8 mmol) and allowed to stir at room temperature for 1 hour. This was then treated with 4-picolyl chloride hydrochloride (6.8 g, 40.9 mmol) and the dark mixture allowed to stir overnight. The mixture was poured into water and extracted twice with ethyl acetate. The combined ethyl acetate extracts were washed with 5% NaOH, three times with water then with brine. Drying over MgSO4 and removal of the solvent under reduced pressure gave the crude product. This was taken up in ethyl acetate, treated with charcoal, filtered, and the solvent removed under reduced pressure to give 5.42 g (62.1%) of the product as an oil; MS-CI 214 (M+1).

후처리

  1. stirringto stir overnight
  2. extractionextracted twice with ethyl acetate
  3. washThe combined ethyl acetate extracts were washed with 5% NaOH, three times with water
  4. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  5. customgave the crude product
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-e990cc9022ba4599a03f84423bda0d6f
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300501B1

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