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

HRID 637287

反応式

HRID 637287 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].[F:13][C:14]1[C:22]([F:23])=[C:21]([F:24])[C:20]([F:25])=[CH:19][C:15]=1[C:16](Cl)=[O:17].S(=O)(=O)(O)O>C(O)C.C1(C)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[F:13][C:14]1[C:22]([F:23])=[C:21]([F:24])[C:20]([F:25])=[CH:19][C:15]=1[C:16]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])=[O:17]

参加物

8

反応物 4

HCID 1118Sulfuric AcidHCID 7761Diethyl MalonateHCID 27336892,3,4,5-Tetrafluorobenzoyl chlorideHCID 5462224Magnesium

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.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. Thereafter, the mixture is heated to 50°-60° C. for a further hour, and cooled to -5° C. to -10° C. with dry ice acetone, and a solution of 212.5 g of 2,3,4,5-tetrafluorobenzoyl chloride (1) in 80 ml of absolute toluene is slowly added dropwise at this temperature. The mixture is stirred for 1 hour at 0° to -5° C., and is allowed to reach room temperature overnight, and a mixture of 400 ml of ice water and 25 ml of concentrated sulphuric acid is allowed to run in whilst cooling with ice. The phases are separated, and extraction with toluene is repeated twice. The combined toluene solutions are washed with saturated NaCl solution and dried with Na2SO4, and the solvent is stripped off in vacuo. 335 g of diethyl 2,3,4,5-tetra-fluorobenzoylmalonate (3) are obtained as a crude product.

後処理

  1. additionis added dropwise at 50°-60° C
  2. temperatureThereafter, the mixture is heated to 50°-60° C. for a further hour
  3. waitto reach room temperature overnight
  4. temperaturecooling with ice
  5. customThe phases are separated
  6. extractionextraction with toluene
  7. washThe combined toluene solutions are washed with saturated NaCl solution
  8. dry with materialdried with Na2SO4

出典と根拠

ORDレコード
ord-c1be0238ed7b471b99e4c73dbf8161fe
出典データセット
uspto-grants-1985_12
特許番号
US04556658

関連ノート

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