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

HRID 1110995

Reaktionsgleichung

Reaktionsgleichung von HRID 1110995
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f81462bf8f0c4a18b16b6ca9e70b12a9
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04977277

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