تفاعل #46731

معادلة التفاعل

BBr3

2-methoxy-4-nonyl benzoic acid

EtOH H2O

→

product

المردود 23.0%

4-Nonyl salicylic acid

المردود 23.0%

المذيبات

HCl

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe reaction mixture was extracted with EtOAc (3×)
2. 2
   تجفيفdried (MgSO4)
3. 3
   ترشيحfiltered
4. 4
   أخرىevaporated to dryness
5. 5
   workup.DISSOLUTIONThe crude ester was dissolved in CH2Cl2 (10 mL)
6. 6
   درجة الحرارةto warm to room temperature overnight
7. 7
   workup.ADDITIONpoured onto H2O
8. 8
   استخلاصextraction with EtOAc
9. 9
   تجفيفdrying (MgSO4)
10. 10
    ترشيحfiltering
11. 11
    أخرىevaporation to dryness and column chromatography (SiO2)

الإجراء التجريبي

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.

المصدر