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

HRID 280099

反応式

HRID 280099 の反応式
[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]

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒2 回HCID 1140Toluene溶媒2 回HCID 5943Carbon Tetrachloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-90bbe3f4fd9e405e8245510b2b0900fc
出典データセット
uspto-grants-1986_05
特許番号
US04588726

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