Hydrochloric Acid → Beta-Carotene

HRID 28277

Reaktionsgleichung

Reaktionsgleichung von HRID 28277
[H-].[Ca+2].[H-].[CH3:4][C:5]1[CH2:10][CH2:9][CH2:8][C:7]([CH3:12])([CH3:11])[C:6]=1/[CH:13]=[CH:14]/[C:15](/[CH3:24])=[CH:16]/[CH:17]=[CH:18]/[C:19](/[CH3:23])=[CH:20]/[CH:21]=O.Cl>O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl>[CH3:4][C:5]1[CH2:10][CH2:9][CH2:8][C:7]([CH3:12])([CH3:11])[C:6]=1/[CH:13]=[CH:14]/[C:15](/[CH3:24])=[CH:16]/[CH:17]=[CH:18]/[C:19](/[CH3:23])=[CH:20]/[CH:21]=[CH:21]/[CH:20]=[C:19](\[CH3:23])/[CH:18]=[CH:17]/[CH:16]=[C:15](\[CH3:24])/[CH:14]=[CH:13]/[C:6]1[C:7]([CH3:12])([CH3:11])[CH2:8][CH2:9][CH2:10][C:5]=1[CH3:4]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 638015RetinalHCID 3033859Calcium hydride

Produkt 1

HCID 5280489Beta-CaroteneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution was prepared by dissolving titanium tetrachloride (1.10 ml, 10.0 mmol) in 25 ml tetrahydrofuran under an inert atmosphere. Calcium hydride (420 mg, 10.0 mmol) was added, and the resulting solution was stirred for two hours at room temperature. A solution of retinal, (1.42 gm, 5.0 mmol) in 5 ml dry tetrahydrofuran was then added, and the reaction was refluxed for three hours. After this, the solution was poured into 50 ml 2 N aqueous hydrochloric acid, and was extracted several times with ether. 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 further purified by chromatography on silica gel. Elution with hexane gave 1.0 gm (75%) beta-carotene, identified by thin-layer chromatographic comparison with an authentic sample, and by its melting point, mp 180°-182°.

Aufarbeitung

  1. customA solution was prepared
  2. temperaturethe reaction was refluxed for three hours
  3. extractionwas extracted several times with ether
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated by solvent removal at the rotary evaporator
  7. customThe residue was further purified by chromatography on silica gel
  8. washElution with hexane

Quellen und Nachweise

ORD-Eintrag
ord-d66dda7157794b6691b8f2df3a19cc62
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04225734

Verknüpfte Notizen

Wird geladen…