Potassium Hydroxide → Diethyl (2-phenylpropan-2-yl)propanedioate

HRID 1722676

反応式

HRID 1722676 の反応式
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9](=[C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])([CH3:11])[CH3:10].[OH-].[K+]>C(O)C>[CH3:10][C:9]([CH:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])([CH3:11])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 14797Potassium HydroxideHCID 81255Diethyl isopropylidenemalonateHCID 178418255HCID 178418255、化合物

生成物 1

HCID 298884Diethyl (2-phenylpropan-2-yl)propanedioate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
50 °C

実験手順

Diethyl (α, α -dimethylbenzyl)malonate was prepared by the conjugate addition of phenyl magnesium bromide to diethyl isopropylidenemalonate as described by C. Holmberg [Liebigs Ann. Chem., 748 (1981)]. A solution of this diester (42.1 g, 0.15 mol) in ethanol (100 ml) was treated by dropwise addition with a solution of potassium hydroxide (8.48 g, 0.13 mol) in 100 ml of ethanol. After heating at 90° C. for 1 h and at 50° C. for 20 h, the reaction mixture was evaporated on the rotary evaporator to a residue. The residue was diluted with water and extracted with ether to remove unreacted starting material. The aqueous phase was cooled to 5° C., acidified to pH 3 with 6N HCl, and extracted with methylene chloride. The organic layer was washed with brine solution and dried over magnesium sulfate. Evaporation of the solvent gave 27.3 g (84%) of liquid product. NMR (CDCl3): 1.05 (3H,t), 1.6 (6H,s), 3.78 (1H,s), 3.96 (2H,m), 7.2-7.4 (5H,m).

後処理

  1. customthe reaction mixture was evaporated on the rotary evaporator to a residue
  2. additionThe residue was diluted with water
  3. extractionextracted with ether
  4. customto remove unreacted
  5. temperatureThe aqueous phase was cooled to 5° C.
  6. extractionextracted with methylene chloride
  7. washThe organic layer was washed with brine solution
  8. dry with materialdried over magnesium sulfate
  9. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-459751a3e09d43048636a2bd3255bf76
出典データセット
uspto-grants-1989_08
特許番号
US04857507

関連ノート

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