Hydrochloric Acid → Ethyl Alpha-oxo-3-(2-nitro-4,5-dichlorophenyl)propanoate

HRID 1070693노트

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HRID 1070693 반응식
[K].[C:2]([O:9][CH2:10][CH3:11])(=[O:8])[C:3]([O:5]CC)=O.[N+:12]([C:15]1[CH:20]=[C:19]([Cl:21])[C:18]([Cl:22])=[CH:17][C:16]=1[CH3:23])([O-:14])=[O:13].Cl>C(OCC)C.O.C(OCC)(=O)C.CCO>[O:5]=[C:3]([CH2:23][C:16]1[CH:17]=[C:18]([Cl:22])[C:19]([Cl:21])=[CH:20][C:15]=1[N+:12]([O-:14])=[O:13])[C:2]([O:9][CH2:10][CH3:11])=[O:8]

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 3437951,2-Dichloro-4-methyl-5-nitrobenzeneHCID 5462222Potassium

생성물 1

HCID 10733409Ethyl Alpha-oxo-3-(2-nitro-4,5-dichlorophenyl)propanoate수율 61,984.102%

시약·촉매·용매 4

HCID 702Ethanol용매HCID 962Water용매HCID 3283Diethyl Ether용매4회HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of potassium (49.2 g, 1.26 mol) in anhydrous diethyl ether (500 ml), a solution of absolute EtOH (319 ml) and anhydrous diethyl ether (260 ml) was added dropwise under nitrogen during a period of four hours. The resulting solution was diluted with anhydrous diethyl ether (1200 mL) and then diethyl oxalate (171 ml, 1.26 mol) was added dropwise in about 30 minutes. To the resulting yellow mixture, a solution of 2-nitro-4,5-dichlorotoluene (260 g, 1.26 mmol), prepared as described by Cohen and Dakin in J. Chem. Soc., 79, 1133, in anhydrous diethyl ether (450 ml) was added dropwise in one hour at RT. Stirring was continued for additional three hours and the dark-brown mixture was settled at RT for two days. The potassium salt was collected by suction and dried to give a dark-brown powder. This was suspended in a mixture of water (400 ml) and ethyl acetate (400 ml), then acidified with 10% HCl. The organic phase was washed with brine, aqueous sat. NaHCO3 and again brine, then it was dried with MgSO4. Evaporation produced 239 g of title compound (781 mmol, yield 62.0%) as a light brown solid that was used as such for the next step, m.p.=92-94° C.

후처리

  1. waitthe dark-brown mixture was settled at RT for two days
  2. customThe potassium salt was collected by suction
  3. customdried
  4. customto give a dark-brown powder
  5. washThe organic phase was washed with brine, aqueous sat. NaHCO3 and again brine
  6. dry with materialit was dried with MgSO4
  7. customEvaporation

출처 및 근거

ORD 기록
ord-7942beb3fef64f6780ed0a0abb81858c
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903117B2

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