تفاعل #2353598

معادلة التفاعل

3-hydroxy-4-methylbenzaldehyde

n-hexylphosphonium bromide

potassium t-butoxide

→

title compound

المردود 88.2%

5-[(1Z)-1-hepten-1-yl]-2-methylphenol

المردود 88.2%

المذيبات

t-butyl methyl ether

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling in ice bath
2. 2
   workup.STIRRINGwas stirred at room temperature for 1.5 hours
3. 3
   غسيلThe solution was washed with dilute hydrochloric acid, water and brine
4. 4
   تجفيفdried over anhydrous sodium sulfate
5. 5
   تركيزconcentrated
6. 6
   أخرىThe obtained residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4)

الإجراء التجريبي

Under an atmosphere of Argon, to a solution of n-hexylphosphonium bromide (1.07 g) in tetrahydrofuran (10 mL) was added potassium t-butoxide (336 mg) at room temperature and the solution was stirred for 30 minutes. After cooling in ice bath, 3-hydroxy-4-methylbenzaldehyde (136 mg) was added to the reaction solution, which was stirred at room temperature for 1.5 hours. The reaction solution was diluted with t-butyl methyl ether. The solution was washed with dilute hydrochloric acid, water and brine, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) to give the title compound (180 mg) having the following physical data.

المصدر