Nitrogen → 5-Chloromethoxy-4-hydroxy-2-nitrobenzaldehyde

HRID 1982217

반응식

HRID 1982217 반응식
[Al+3].[Cl-:2].[Cl-].[Cl-].[CH2:5]1[O:9][C:8]2[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[C:12]([CH:14]=[O:15])=[CH:13][C:7]=2[O:6]1.N#N.O>ClC(Cl)C>[Cl:2][CH2:5][O:6][C:7]1[C:8]([OH:9])=[CH:10][C:11]([N+:16]([O-:18])=[O:17])=[C:12]([CH:13]=1)[CH:14]=[O:15]

참가 물질

6

반응물 4

HCID 947NitrogenHCID 962WaterHCID 128406-Nitro-1,3-benzodioxole-5-carboxaldehydeHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 114247525-Chloromethoxy-4-hydroxy-2-nitrobenzaldehyde수율 97%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매2회

실험 절차

AlCl3 (6 g) and dry dichloroethane (15 ml) are added to a three-neck round bottom flask, which has been purged with N2, and the dispersion is cooled to -5°. A solution of 6-nitropiperonal (3 g; 0.0154 mol) (available from Aldrich Chemical Co.) in 12 ml dry dichloroethane is added to the dispersion, in one portion, while the temperature and N2 atmosphere are maintained. The reaction mixture is stirred for 1.25 hours, and 100 ml H2O (0°) is added. The emulsion is stirred for 15 minutes, then extracted with 3×100 ml ethyl acetate. The combined organics are washed with saturated NaCl, then dried over Na2SO4. After filtration, the ethyl acetate is removed at reduced pressure. Recrystallization from ethyl acetate gives 3.45 g (97%) of (10): mp 160°-161° C.

후처리

  1. customwhich has been purged with N2
  2. temperaturethe dispersion is cooled to -5°
  3. temperatureare maintained
  4. stirringThe emulsion is stirred for 15 minutes
  5. extractionextracted with 3×100 ml ethyl acetate
  6. washThe combined organics are washed with saturated NaCl
  7. dry with materialdried over Na2SO4
  8. filtrationAfter filtration
  9. customthe ethyl acetate is removed at reduced pressure
  10. customRecrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-df8b27b8e1e74d54a1d595e591787cbd
출처 데이터셋
uspto-grants-1986_06
특허 번호
US04595765

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