Nitric Acid → 4-(2-Chloroethoxy)-5-methoxy-2-nitrobenzaldehyde

HRID 989390ノート

反応式

HRID 989390 の反応式
[N+:1]([O-:4])(O)=[O:2].[Cl:5][CH2:6][CH2:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[O:17][CH3:18]>ClCCCl>[Cl:5][CH2:6][CH2:7][O:8][C:9]1[C:10]([O:17][CH3:18])=[CH:11][C:12]([CH:13]=[O:14])=[C:15]([N+:1]([O-:4])=[O:2])[CH:16]=1

参加物

4

反応物 2

HCID 944Nitric AcidHCID 107750234-(2-Chloroethoxy)-3-methoxybenzaldehyde

生成物 1

HCID 219563824-(2-Chloroethoxy)-5-methoxy-2-nitrobenzaldehyde収率 40%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
-10 °C

実験手順

Fuming nitric acid (10 mL) is added dropwise to a −40° C. suspension of 5.00 g (23.36 mmol) of 4-(2-chloroethoxy)-3-methoxybenzaldehyde (Milbank, J. B. J., et. al., J. Med. Chem., 42(4), 649-658, 1999) in 23 mL of 1,2-dichloroethane. The reaction mixture is slowly allowed to warm to −10° C. The mixture is poured onto 300 mL of ice water and then extracted with ethyl acetate. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo. Diethyl ether is added to the residue and the pale yellow solid is collected by filtration to provide 2.43 g (40%) of 4-(2-chloroethoxy)-5-methoxy-2-nitrobenzaldehyde, mp 148-150° C.

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additionDiethyl ether is added to the residue
  6. filtrationthe pale yellow solid is collected by filtration

出典と根拠

ORDレコード
ord-072dc079392344c8bbaff9ac7698360b
出典データセット
uspto-grants-2003_10
特許番号
US06638929B2

反応ノート

読み込み中…