Hydrochloric Acid → Beta-Carotene

HRID 28277

반응식

HRID 28277 반응식
[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]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 638015RetinalHCID 3033859Calcium hydride

생성물 1

HCID 5280489Beta-Carotene수율 75%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-d66dda7157794b6691b8f2df3a19cc62
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04225734

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