Sulfuric Acid → 1,3-Diethyl 2-(2,3,4,5-tetrafluorobenzoyl)propanedioate

HRID 280099

반응식

HRID 280099 반응식
[Mg].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C(=O)=O.CC(C)=O.[F:20][C:21]1[C:29]([F:30])=[C:28]([F:31])[C:27]([F:32])=[CH:26][C:22]=1[C:23](Cl)=[O:24].S(=O)(=O)(O)O>C(O)C.C1(C)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[F:20][C:21]1[C:29]([F:30])=[C:28]([F:31])[C:27]([F:32])=[CH:26][C:22]=1[C:23]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])=[O:24]

참가 물질

9

반응물 5

HCID 1118Sulfuric AcidHCID 7761Diethyl MalonateHCID 27336892,3,4,5-Tetrafluorobenzoyl chlorideHCID 5462224MagnesiumHCID 18522661Acetone cardice

생성물 1

HCID 135649731,3-Diethyl 2-(2,3,4,5-tetrafluorobenzoyl)propanedioate수율 99.7%

시약·촉매·용매 3

HCID 702Ethanol용매2회HCID 1140Toluene용매2회HCID 5943Carbon Tetrachloride용매

실험 절차

24.3 g of magnesium turnings are suspended in 50 ml of anhydrous ethanol. 5 ml of carbon tetrachloride are added and, when the reaction has started, a mixture of 160 g of diethyl malonate, 100 ml of absolute ethanol and 400 ml of anhydrous toluene is added dropwise at 50°-60° C. The mixture is then heated at 50°-60° C. for 1 hour, cooled to 5° C. to -10° C. with dry ice/acetone and, at this temperature, a solution of 212.5 g of 2,3,4,5-tetrafluorobenzoyl chloride in 80 ml of absolute toluene is slowly added dropwise. The mixture is stirred at 0° to -5° C. for 1 hour, allowed to reach room temperature overnight, and, while cooling in ice, a mixture of 400 ml of ice-water and 25 ml of concentrated sulphuric acid is allowed to run in. The phases are separated and two further extractions with toluene are carried out. The combined toluene solutions are washed with saturated NaCl solution, dried with Na2SO4, and the solvent is removed in vacuo. 335 g of diethyl 2,3,4,5-tetrafluorobenzoylmalonate are obtained as a crude product.

후처리

  1. additionis added dropwise at 50°-60° C
  2. temperatureThe mixture is then heated at 50°-60° C. for 1 hour
  3. waitto reach room temperature overnight
  4. temperaturewhile cooling in ice
  5. customThe phases are separated
  6. extractiontwo further extractions with toluene
  7. washThe combined toluene solutions are washed with saturated NaCl solution
  8. dry with materialdried with Na2SO4
  9. customthe solvent is removed in vacuo

출처 및 근거

ORD 기록
ord-90bbe3f4fd9e405e8245510b2b0900fc
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04588726

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