Hydrochloric Acid → 3-Hydroxy-4-(1-oxo-2-methylbutyl)phenyl 4-(4'-octyloxyphenyl)benzoate

Participants

Reaction Steps

0.5 g of 3-hydroxy-4-(1-oxo-2-methylbutyl)phenol prepared by the process described in (1) was dissolved in 15 ml of anhydrous pyridine, to which added was a solution of 0.7 g of 4-(4'-octyloxyphenyl)benzoic acid chloride dissolved in 20 ml of anhydrous methylene chloride dropwisely over a period of about one hour under stirring. The reaction mixture was stirred at the room temperature for additional 40 hours to proceed the reaction. Then, the reaction mixture was added to 300 ml of dilute hydrochloric acid solution. After adding 50 ml of chloroform and 50 ml of ethyl ether, followed by shaking, the organic phase was separated from the aqueous phase. The organic phase was rinsed with a dilute hydrochloric acid solution for two times, rinsed with an aqueous solution of NaHCO3 for one time, and then rinsed with a 3% aqueous solution of NaCl for three times. Anhydrous Na2SO4 was added to the organic phase to dry the same. After removing the drying agent by filtration, the solvent was distilled off to obtain a crude product which was refined through silica gel column chromatography while using chlorofrom as the eluent. The thus obtained product was recrystallized from a mixed solvent composed of 10 parts by volume of chloroform and 90 parts by volume of n-hexane. As a result, 0.08 g of 3-hydroxy-4-(1-oxo-2-methylbutyl)phenyl 4-(4'-octyloxyphenyl)benzoate was obtained.

Provenance & Evidence