反应详情

A mixture of 10 g (0.06 mol) of 3,5-dihydroxybenzoic acid methyl ester, 16.2 ml (0.06 mol) of 1-bromotetradecane and 8.2 g (0.06 mol) of potassium carbonate in 200 ml of acetone and 20 ml of DMF was stirred at reflux under argon for 24 hours, After the usual workup, the crude product was triturated with hot methylene chloride and filtered. The filtrate was concentrated at reduced pressure and the solid residue was recrystallized from methylene chloride-methanol to give the 3,5-dialkylated product. The filtrate was concentrated and the residue was purified by HPLC using 15% ethyl acetatehexane to give 7.3 g (34% yield, mp 92°-94°) of 3-hydroxy-5-(tetradecyloxy)benzoic acid methyl ester. The nmr spectra was consistent with the structure.

1. temperatureat reflux under argon for 24 hours
2. customAfter the usual workup, the crude product was triturated with hot methylene chloride
3. filtrationfiltered
4. concentrationThe filtrate was concentrated at reduced pressure
5. customthe solid residue was recrystallized from methylene chloride-methanol
6. customto give the 3,5-dialkylated product
7. concentrationThe filtrate was concentrated
8. customthe residue was purified by HPLC