Reacción #46731

Ecuación de reacción

BBr3

2-methoxy-4-nonyl benzoic acid

EtOH H2O

→

product

Rendimiento 23.0%

4-Nonyl salicylic acid

Rendimiento 23.0%

Disolventes

HCl

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe reaction mixture was extracted with EtOAc (3×)
2. 2
   Secadodried (MgSO4)
3. 3
   Filtraciónfiltered
4. 4
   Otroevaporated to dryness
5. 5
   workup.DISSOLUTIONThe crude ester was dissolved in CH2Cl2 (10 mL)
6. 6
   Temperaturato warm to room temperature overnight
7. 7
   workup.ADDITIONpoured onto H2O
8. 8
   Extracciónextraction with EtOAc
9. 9
   Secadodrying (MgSO4)
10. 10
    Filtraciónfiltering
11. 11
    Otroevaporation to dryness and column chromatography (SiO2)

Procedimiento

A solution of 2-methoxy-4-nonyl benzoic acid (600 mg; 2.15 mmol) was refluxed overnight in 6 M HCl [50% (w/w) EtOH/H2O; 35 mL). The reaction mixture was extracted with EtOAc (3×) dried (MgSO4), filtered and evaporated to dryness. The crude ester was dissolved in CH2Cl2 (10 mL), cooled to −10° C. and then added 1 M BBr3 (CH2Cl2; 10 mL; 10 mmol). The reaction mixture was allowed to warm to room temperature overnight and then poured onto H2O. Succeeding extraction with EtOAc, drying (MgSO4), filtering, evaporation to dryness and column chromatography (SiO2) yielded 130 mg (23%) product. Mp. 94-97° C.

Fuente