Thionyl Chloride → 4-(Dodecyloxy)benzoyl chloride

Beteiligte Stoffe

Reaktionsschritte

p-n-Dodecyloxybenzoic acid (8 g) together with thionyl chloride (20 ml) were heated under reflux for 2 hours, followed by distilling off excess thionyl chloride to obtain p-n-dodecyloxybenzoic acid chloride, which was made up into a toluene solution thereof without any particular purification. On the other hand, optically active hydroquinonemono(2-methylbutyl) ether (4.7 g) obtained above in the item (I) was dissolved in pyridine (30 ml). To this solution kept at 0° C. was dropwise added the toluene solution of p-n-dodecyloxybenzoic acid chloride obtained above, followed by heating the mixture at 90° C. for 2 hours for reaction, separating the resulting esterified substance in a conventional manner, and twice repeating recrystallization to obtain colorless crystals of p-n-dodecyloxybenzoic acid p'-(2-methylbutyloxy)phenyl ester (C-SC* point, 50.5° C.; SC*-SA point, 51.2° C.; SA-I point, 65° C.; and [α]D25° =+5.2° (as measured in chloroform solution)) (6.5 g). Further its elemental analysis values accorded well with its theoretical values as follows:

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