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

HRID 580441

반응식

HRID 580441 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 102.6%

시약·촉매·용매 3

HCID 702Ethanol용매2회HCID 1140Toluene용매2회HCID 5943Carbon Tetrachloride용매

반응 조건

온도
60 °C

실험 절차

20.1 g of magnesium chips are suspended in 40 ml of anhydrous ethanol. 4 ml of carbon tetrachloride are added and, when the reaction has started, a mixture of 132.2 g of diethyl malonate, 80 ml of absolute ethanol and 320 ml of anhydrous toluene are added dropwise at 50°-60° C. When the reaction has subsided, the mixture is heated at 60° C. for a further 2 hours and cooled to -5° C. to -10° C. with dry ice/acetone, and a solution of 175.5 g of 2,3,4,5-tetrafluorobenzoyl chloride in 100 ml of absolute toluene is slowly added dropwise at this temperature. The mixture is stirred at 0° C. to -5° C. for 1 hour and is allowed to come to room temperature overnight, and a mixture of 350 ml of ice-wter and 50 ml of concentrated sulphuric acid is run in, while cooling with ice. The phases are separated and the aqueous phase is after-extracted twice with toluene. The combined toluene solutions are washed with saturated sodium chloride solution, and dried with sodium sulphate and the solvent is stripped off in vacuo. 284.8 g of diethyl 2,3,4,5-tetrafluoro-benzoyl-malonate are obtained as the crude product.

후처리

  1. additionare added dropwise at 50°-60° C
  2. waitto come to room temperature overnight
  3. temperaturewhile cooling with ice
  4. customThe phases are separated
  5. extractionthe aqueous phase is after-extracted twice with toluene
  6. washThe combined toluene solutions are washed with saturated sodium chloride solution
  7. dry with materialdried with sodium sulphate

출처 및 근거

ORD 기록
ord-cd1a8c0b4cad4de7af2b35fed6368cd6
출처 데이터셋
uspto-grants-1988_06
특허 번호
US04753925

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