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

HRID 249404

反応式

HRID 249404 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 congugate 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 mole) in ethanol (100 mL) was treated by dropwise addition with a solution of potassium hydroxide (8.48 g, 0.13 mole) 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-33deeba48eb840eb86a3ae864677223c
出典データセット
uspto-grants-1993_05
特許番号
US05214129

関連ノート

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