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

HRID 380182ノート

反応式

HRID 380182 の反応式
[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

参加物

8

反応物 4

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

生成物 1

HCID 167689982-(Pyridin-4-ylmethoxy)benzaldehyde収率 62.1%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e990cc9022ba4599a03f84423bda0d6f
出典データセット
uspto-grants-2001_10
特許番号
US06300501B1

反応ノート

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