Hydrochloric Acid → Beta-Carotene

HRID 28269

反応式

HRID 28269 の反応式
[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]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 638015Retinal

生成物 1

HCID 5280489Beta-Carotene収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A slurry of titanium trichloride (1.54 gm, 10.0 mmol) in 30 ml dry tetrahydrofuran was prepared under an inert atmosphere (nitrogen or argon), and powdered lithium aluminum hydride (190 mg. 5.0 mmol) was cautiously added. The resulting solution was stirred for two hours at room temperature to form the Ti(II) reagent, and a solution of retinal (1.42 gm, 5.0 mmol) in 5 ml dry tetrahydrofuran was added. The solution was stirred a further fifteen hours at room temperature, and then poured into 50 ml 2 N aqueous hydrochloric acid. The solution was extracted several times with ether, and 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 purified by chromatography on silica gel. Elution with hexane gave 1.14 gm (85% yield) beta-carotene which was identified by thin-layer chromatographic comparison with an authentic sample, by its characteristic ultraviolet spectrum, and by its melting point: mp 180°-182°.

後処理

  1. extractionThe solution was extracted several times with ether
  2. washwashed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated by solvent removal at the rotary evaporator
  5. customThe residue was purified by chromatography on silica gel
  6. washElution with hexane

出典と根拠

ORDレコード
ord-1b32108d7b634a20a2e75a74c36c4bdc
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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