Hydrochloric Acid → Beta-Carotene

HRID 28269

Reaktionsgleichung

Reaktionsgleichung von HRID 28269
[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 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A slurry of titanium trichloride (1.54 gm, 10.0 mmol) in 30 ml dry tetrahydrofuran was prepared under an inert atmosphere (nitrogen or argon), and powdered lithium aluminum hydride (190 mg. 5.0 mmol) was cautiously added. The resulting solution was stirred for two hours at room temperature to form the Ti(II) reagent, and a solution of retinal (1.42 gm, 5.0 mmol) in 5 ml dry tetrahydrofuran was added. The solution was stirred a further fifteen hours at room temperature, and then poured into 50 ml 2 N aqueous hydrochloric acid. The solution was extracted several times with ether, and the ether extracts were combined, washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated by solvent removal at the rotary evaporator. The residue was purified by chromatography on silica gel. Elution with hexane gave 1.14 gm (85% yield) beta-carotene which was identified by thin-layer chromatographic comparison with an authentic sample, by its characteristic ultraviolet spectrum, and by its melting point: mp 180°-182°.

Aufarbeitung

  1. extractionThe solution was extracted several times with ether
  2. washwashed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated by solvent removal at the rotary evaporator
  5. customThe residue was purified by chromatography on silica gel
  6. washElution with hexane

Quellen und Nachweise

ORD-Eintrag
ord-1b32108d7b634a20a2e75a74c36c4bdc
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04225734

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