Reacción #2353598

Ecuación de reacción

3-hydroxy-4-methylbenzaldehyde

n-hexylphosphonium bromide

potassium t-butoxide

→

title compound

Rendimiento 88.2%

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

Rendimiento 88.2%

Disolventes

t-butyl methyl ether

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente