Hydrochloric Acid → Beta-Carotene

HRID 28271

반응식

HRID 28271 반응식
[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]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 638015Retinal

생성물 1

HCID 5280489Beta-Carotene수율 20%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2ca4736e40054782a50c85c5dc13f772
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04225734

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