Isopropanol → Isopropyl Hydrogen Phenylmalonate

HRID 36902

Reaktionsgleichung

Reaktionsgleichung von HRID 36902
[C:1]1([CH:7]([C:11]([OH:13])=[O:12])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH:18](O)([CH3:20])[CH3:19]>CCOCC.CN(C)C=O>[C:1]1([CH:7]([C:11]([OH:13])=[O:12])[C:8]([O:10][CH:18]([CH3:20])[CH3:19])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 3

HCID 3776IsopropanolHCID 24386Thionyl ChlorideHCID 75791Phenylmalonic acid

Produkt 1

HCID 19042994Isopropyl Hydrogen PhenylmalonateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Phenylmalonic acid (13.5 g, 0.07 mol ) in dry ether (40 mL) was treated with thionyl chloride (8.92 g, 5.4 mL, 0.07 mol) and one drop of N,N-dimethylformamide. The mixture was heated at 40°-50° C. for 3 hours. The clear solution was evaporated under reduced pressure to remove any residual thionyl chloride. The oily residue was redissolved in dry ether (40 mL), and the solution was treated with isopropyl alcohol (0.075 mol, 5.76 mL), refluxed for 2 hours and worked up as before to give the titled compound.

Aufarbeitung

  1. temperatureThe mixture was heated at 40°-50° C. for 3 hours
  2. customThe clear solution was evaporated under reduced pressure
  3. customto remove any residual thionyl chloride
  4. dissolutionThe oily residue was redissolved in dry ether (40 mL)
  5. temperaturerefluxed for 2 hours

Quellen und Nachweise

ORD-Eintrag
ord-af73ff0456864c18a081b75ef0069f5f
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05418244

Verknüpfte Notizen

Wird geladen…