Acetone → 1,3-Propanediol, 2-(4-pentenyl)-

HRID 2254981

Reaktionsgleichung

Reaktionsgleichung von HRID 2254981
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([CH:12]([C:18](OCC)=[O:19])[C:13](OCC)=[O:14])[CH2:8][CH2:9][CH:10]=[CH2:11].CC(C)=O.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:7]([CH:12]([CH2:18][OH:19])[CH2:13][OH:14])[CH2:8][CH2:9][CH:10]=[CH2:11]

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 361718Diethyl 2-pent-4-enylpropanedioateHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 110947511,3-Propanediol, 2-(4-pentenyl)-Ausbeute 84,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A suspension of 13.8 g of lithium aluminium hydride in 500 ml of tetrahydrofuran was treated dropwise under nitrogen at 0°-5° C. within 1 hour with a solution of 33.2 g of diethyl (4-pentenyl)malonate in 125 ml of tetrahydrofuran. The mixture was stirred overnight at room temperature and then heated to boiling for 3 hours. After cooling there were cautiously added dropwise to the reaction mixture firstly 25 ml of acetone and then 25 ml of saturated sodium hydrogen carbonate solution. The resulting slurry was suction filtered and the residue on the suction filter was washed four times with tetrahydrofuran. Concentration of the filtrate gave 17.8 g of 2-(4-pentenyl)-1,3-propanediol (purity 89%) as a yellow liquid.

Aufarbeitung

  1. temperatureheated
  2. waitto boiling for 3 hours
  3. temperatureAfter cooling there
  4. filtrationfiltered
  5. filtrationthe residue on the suction filter
  6. washwas washed four times with tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag
ord-ccdd6c6ec8f844d7b3e4ce94154a2b28
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05238602

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