Hydrochloric Acid → 2-Pentyl-1,3-propanediol

HRID 1494661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1494661
[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][CH2:10][CH3:11].Cl>O1CCCC1.O>[CH2:7]([CH:12]([CH2:18][OH:19])[CH2:13][OH:14])[CH2:8][CH2:9][CH2:10][CH3:11]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 80167Diethyl pentylmalonateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 1175092-Pentyl-1,3-propanediolAusbeute 67,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

35 g (0.92 mol) of lithium aluminum hydride was dispersed in 420 cm2 of anhydrous tetrahydrofuran (THF) and 193 g (0.84 mol) of diethyl pentylmalonate was added drop-wise to the dispersion while stirring at a speed to gently reflux the THF. The solution was refluxed and stirred for 3 hours. The product of the reaction was cooled with water and THF containing 10% water was added until the mixture ceased to foam. 500 cm2 of concentrated hydrochloric acid was added. The oily layer was separated and the water layer was extracted three times with 200 cm3 of ether. The oily layer and the ether layers were combined and washed with a saturated aqueous solution of sodium chloride. The ether layer was dried with anhydrous sodium sulfate and boiled to distil off the ether. The residue of the distillation was subjected to vacuum distillation (b.p. 120° C./2 Torrs) to yield 83 g (0.57 mol) of 2-pentylpropane-1,3-diol.

Aufarbeitung

  1. additionwas added drop-wise to the dispersion
  2. temperatureThe solution was refluxed
  3. stirringstirred for 3 hours
  4. additionwas added until the mixture
  5. customThe oily layer was separated
  6. extractionthe water layer was extracted three times with 200 cm3 of ether
  7. washwashed with a saturated aqueous solution of sodium chloride
  8. dry with materialThe ether layer was dried with anhydrous sodium sulfate
  9. customto distil off the ether
  10. distillationThe residue of the distillation
  11. distillationwas subjected to vacuum distillation (b.p. 120° C./2 Torrs)

Quellen und Nachweise

ORD-Eintrag
ord-a4299ef4f940424589913e39617a5011
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05026879

Notizen zur Reaktion

Wird geladen…