Droctil,Ciba Geigy,Italy,1971
p-Hydroxy-benzoic acid methyl ester was subjected to a condensation reaction
with 3-hexoxy-2-hydroxy-1-chloropropane in the presence of sodium ethylate
and ethanol as a solvent, yielding p-(3-hexoxy-2-hydroxy)-propoxy-benzoic
acid methyl ester.
62 g of this intermediate product were admixed with 250 cc of 2N sodium
hydroxide and the resulting mixture was refluxed for three hours. The reaction
mixture was allowed to cool and was made acid with concentrated
hydrochloric acid while cooling it on ice. An oil separated out which was
extracted with ether. The ether extract solution was dried over sodium sulfate
and then the ether was distilled off, leaving a crystalline mass as a residue.
The crystalline product was recrystallized from a mixture of benzene and
petroleum ether, yielding a compound having a MP of 68°C.
