Reacción #81716

Ecuación de reacción

methyl 2-(4'-hydroxymethylphenyl)benzoate

thionyl chloride

→

title compound

Rendimiento 88.0%

methyl 2-(4'-chloromethylphenyl)benzoate

Rendimiento 88.0%

Disolventes

methylene chloride

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat room temperature
2. 2
   Temperaturaunder reflux
3. 3
   Temperaturaby heating for 5 hours
4. 4
   OtroAfter the reaction liquid
5. 5
   Temperaturawas cooled
6. 6
   Concentraciónconcentrated
7. 7
   workup.ADDITIONa saturated aqueous solution of sodium hydrogencarbonate was added
8. 8
   Extracciónfollowed by the extraction with methylene chloride
9. 9
   LavadoThe organic phase was washed with water
10. 10
    Otrodried
11. 11
    Concentraciónsubjected to vacuum concentration
12. 12
    OtroThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

Procedimiento

2.0 g (8.25 mmol) of methyl 2-(4'-hydroxymethylphenyl)benzoate was dissolved in 1.31 g of pyridine and methylene chloride (20 ml). 1.47 g (12.4 mmol) of thionyl chloride was dropwise added thereto at room temperature, followed by stirring as such for 16 hours and under reflux by heating for 5 hours. After the reaction liquid was cooled and concentrated, a saturated aqueous solution of sodium hydrogencarbonate was added thereto, followed by the extraction with methylene chloride. The organic phase was washed with water, dried and subjected to vacuum concentration. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 1.89 g of the title compound as an oil (yield 88%).

Fuente