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

HRID 989390노트

반응식

HRID 989390 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 219563824-(2-Chloroethoxy)-5-methoxy-2-nitrobenzaldehyde수율 40%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

반응 조건

온도
-10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-072dc079392344c8bbaff9ac7698360b
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06638929B2

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