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

HRID 1086868

반응식

HRID 1086868 반응식
[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

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 81255Diethyl isopropylidenemalonateHCID 178418255HCID 178418255, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
50 °C

실험 절차

Diethyl (alpha,alpha-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).

후처리

  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

출처 및 근거

ORD 기록
ord-cf10ad1275264a34b1a8b8fb843b3ddc
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05032577

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