Hydrochloric Acid → Beta-Carotene

HRID 28276

반응식

HRID 28276 반응식
[BH4-].[Li+].[CH3:3][C:4]1[CH2:9][CH2:8][CH2:7][C:6]([CH3:11])([CH3:10])[C:5]=1/[CH:12]=[CH:13]/[C:14](/[CH3:23])=[CH:15]/[CH:16]=[CH:17]/[C:18](/[CH3:22])=[CH:19]/[CH:20]=O.Cl>O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl>[CH3:3][C:4]1[CH2:9][CH2:8][CH2:7][C:6]([CH3:11])([CH3:10])[C:5]=1/[CH:12]=[CH:13]/[C:14](/[CH3:23])=[CH:15]/[CH:16]=[CH:17]/[C:18](/[CH3:22])=[CH:19]/[CH:20]=[CH:20]/[CH:19]=[C:18](\[CH3:22])/[CH:17]=[CH:16]/[CH:15]=[C:14](\[CH3:23])/[CH:13]=[CH:12]/[C:5]1[C:6]([CH3:11])([CH3:10])[CH2:7][CH2:8][CH2:9][C:4]=1[CH3:3]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 638015RetinalHCID 4148881Lithium borohydride

생성물 1

HCID 5280489Beta-Carotene수율 60%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 8028Tetrahydrofuran용매

실험 절차

A solution was prepared by dissolving titanium tetrachloride (1.10 ml, 10.0 mmol) in 25 ml dry tetrahydrofuran under an inert atmosphere. Lithium Borohydride (110 mg, 5.0 mmol) was added, and the resulting solution was stirred at 50° for two hours. A solution of retinal (1.42 gm, 5.0 mmol) 5 ml dry tetrahydrofuran was added, and the reaction was refluxed for four 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 0.8 gm (60%) beta-carotene, identified by comparison with an authentic sample; mp 180°-182°.

후처리

  1. customA solution was prepared
  2. temperaturethe reaction was refluxed for four 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-a2a98f01d03845299abd3c969e826119
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04225734

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