Hydrochloric Acid → Beta-Carotene

HRID 28277

反応式

HRID 28277 の反応式
[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]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 638015RetinalHCID 3033859Calcium hydride

生成物 1

HCID 5280489Beta-Carotene収率 75%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-d66dda7157794b6691b8f2df3a19cc62
出典データセット
uspto-grants-1980_09
特許番号
US04225734

関連ノート

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