تفاعل #56555

معادلة التفاعل

Calcium hydride

retinal

hydrochloric acid

→

beta-carotene

المردود 75.0%

المذيبات

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىA solution was prepared
2. 2
   درجة الحرارةthe reaction was refluxed for three hours
3. 3
   استخلاصwas extracted several times with ether
4. 4
   غسيلwashed with saturated aqueous sodium chloride solution
5. 5
   تجفيفdried over magnesium sulfate
6. 6
   تركيزconcentrated by solvent removal at the rotary evaporator
7. 7
   أخرىThe residue was further purified by chromatography on silica gel
8. 8
   غسيلElution with hexane

الإجراء التجريبي

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°.

المصدر