Réaction #46731

Équation de réaction

BBr3

2-methoxy-4-nonyl benzoic acid

EtOH H2O

→

product

Rendement 23.0%

4-Nonyl salicylic acid

Rendement 23.0%

Solvants

HCl

Conditions de réaction

Traitement

1. 1
   ExtractionThe reaction mixture was extracted with EtOAc (3×)
2. 2
   Séchagedried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Autreevaporated to dryness
5. 5
   workup.DISSOLUTIONThe crude ester was dissolved in CH2Cl2 (10 mL)
6. 6
   Températureto warm to room temperature overnight
7. 7
   workup.ADDITIONpoured onto H2O
8. 8
   Extractionextraction with EtOAc
9. 9
   Séchagedrying (MgSO4)
10. 10
    Filtrationfiltering
11. 11
    Autreevaporation to dryness and column chromatography (SiO2)

Mode opératoire

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.

Source