반응 #46731

반응 방정식

BBr3

2-methoxy-4-nonyl benzoic acid

EtOH H2O

→

product

수율 23.0%

4-Nonyl salicylic acid

수율 23.0%

용매

HCl

반응 조건

후처리

1. 1
   추출The reaction mixture was extracted with EtOAc (3×)
2. 2
   건조dried (MgSO4)
3. 3
   여과filtered
4. 4
   기타evaporated to dryness
5. 5
   workup.DISSOLUTIONThe crude ester was dissolved in CH2Cl2 (10 mL)
6. 6
   온도to warm to room temperature overnight
7. 7
   workup.ADDITIONpoured onto H2O
8. 8
   추출extraction with EtOAc
9. 9
   건조drying (MgSO4)
10. 10
    여과filtering
11. 11
    기타evaporation to dryness and column chromatography (SiO2)

실험 절차

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.

출처