Hydrochloric Acid → Beta-Carotene

HRID 28271

Reaktionsgleichung

Reaktionsgleichung von HRID 28271
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:21])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:20])=[CH:17]/[CH:18]=O.Cl>O1CCCC1>[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:21])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:20])=[CH:17]/[CH:18]=[CH:18]/[CH:17]=[C:16](\[CH3:20])/[CH:15]=[CH:14]/[CH:13]=[C:12](\[CH3:21])/[CH:11]=[CH:10]/[C:3]1[C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][CH2:7][C:2]=1[CH3:1]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 638015Retinal

Produkt 1

HCID 5280489Beta-CaroteneAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A slurry of titanium trichloride (770 mg, 5.0 mmol) in 20 ml dry tetrahydrofuran was prepared under an inert atmosphere (nitrogen or argon), and magnesium turnings (120 mg, 5.0 mmol) were added. The resulting mixture was refluxed overnight to form the Ti(II) reagent, and a solution of retinal (710 mg, 2.5 mmol) in 5 ml dry tetrahydrofuran was added. After refluxing for two hours, the solution was poured into 50 ml 2 N aqueous hydrochloric acid and extracted several times with ether. The ether extracts were combined, washed with saturated aqueous sodium chloride solution, dried sulfate, and concentrated by solvent removal at the rotary evaporator. The residue was purified by chromatography over silica gel. Elution with hexane gave 130 mg (20% yield) beta-carotene identified by thin-layer chromatographic comparison with an authentic sample, and by its characteristic ultraviolet spectrum.

Aufarbeitung

  1. temperatureAfter refluxing for two hours
  2. extractionextracted several times with ether
  3. washwashed with saturated aqueous sodium chloride solution, dried sulfate
  4. concentrationconcentrated by solvent removal at the rotary evaporator
  5. customThe residue was purified by chromatography over silica gel
  6. washElution with hexane

Quellen und Nachweise

ORD-Eintrag
ord-2ca4736e40054782a50c85c5dc13f772
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04225734

Verknüpfte Notizen

Wird geladen…