Water → 4-Octyloxycarbonyloxybenzoic acid 4-(1-methylheptyloxycarbonyl)phenyl ester

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Reaction Steps

Optically active 4-(1-methylheptyloxycarbonyl)phenol (10 g, 0.04 mol) was dissolved in pyridine (70 ml), followed by dropwise adding to the solution, under cooling, 4-octyloxycarbonyloxybenzoic chloride (11.4 g, 0.035 mol) prepared in the same manner as in the paragraph (ii) of Example 1, agitating the mixture at 50°-60° C. for 2 hours, placing water and toluene in the reaction solution after completion of the reaction, sufficiently agitating the mixture, washing the separated toluene layer with 6N--HCl, then with 2N-NaOH aqueous solution, further with water until the washing water became neutral, drying the resulting toluene layer with anhydrous sodium sulfate, distilling off toluene to obtain a raw objective product, and recrystallizing this product from ethanol to obtain optically active 4-octyloxycarbonyloxybenzoic acid 4-(1-methylheptyloxycarbonyl)phenyl ester (5.2 g), which exhibited no liquid crystal phase and had a m.p. of 33.0° C. Further, by replacing octyl chloroformate used, by other alkyl chloroformates, various optically active 4-alkyloxycarbonyloxybenzoic acid 4-(1-methyl-heptyloxycarbonyl)phenyl esters are obtained. The phase transition points thereof are shown in Tables 1 and 2.

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