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

HRID 280099

Reaktionsgleichung

Reaktionsgleichung von HRID 280099
[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]

Komponenten

9

Edukt 5

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

Produkt 1

HCID 135649731,3-Diethyl 2-(2,3,4,5-tetrafluorobenzoyl)propanedioateAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittel2×HCID 1140TolueneLösungsmittel2×HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-90bbe3f4fd9e405e8245510b2b0900fc
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04588726

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