4-Hydroxybenzaldehyde → p-Octyloxycarbonyloxybenzaldehyde

Participants

Reaction Steps

Octyl chloroformate (23.1 g, 0.12 mol) was added to and reacted with a solution of p-hydroxybenzaldehyde (III) (16 g, 0.18 mol) dissolved in dry pyridine (100 ml), followed by allowing the reaction mixture to stand overnight, thereafter extracting it with toluene, washing the organic layer with 6N-hydrochloric acid, then with 2N-NaOH aqueous solution and further with water until the washing water became neutral, and distilling off toluene to obtain p-octyloxycarbonyloxybenzaldehyde (IV) (33.2 g), dissolving this compound (20.5 g, 0.07 mol) in acetic acid (60 ml), dropwise adding a solution of anhydrous chromic acid (14 g, 0.14 mol) dissolved in water (11 ml) and acetic (17 ml) to the above solution being agitated, keeping the inner temperature at 40° C. on a water bath for 4 hours after completion of the dropwise addition, thereafter cooling the reaction mixture, adding water (300 ml), filtering the deposited crystals, recrystallizing from ethanol to obtain p-hexyloxycarbonyloxybenzoic acid (V) (7 g), adding thereto thionyl chloride (10 ml), heating the mxiture under reflux for one hour, and distilling off excess thionyl chloride to obtain the objective p-hexyloxycarbonyloxybenzoic acid chloride (VI) (7.5 g).

Provenance & Evidence