Acetic Acid → 12-(3,5-Di-tert-butyl-4-hydroxyphenylthio)dodecanoic acid

Beteiligte Stoffe

Reaktionsschritte

To a solution of 2,6-di-tert-butyl-4-mercaptophenol (II) (477 mg; 2 mmol) in dry ethanol (20 ml), water containing 12-bromododecanoic acid (558 mg; 2 mmol) and 97 % sodium hydroxide (250 mg; 6 mmol) was added, and the resultant mixture was allowed to stand at room temperature for 20 hours. The reaction mixture was made acidic with 10 aqueous acetic acid and extracted with ethyl acetate. The extract was washed two times with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product thus obtained was chromatographed on silica gel and eluted with ethyl acetate. The collected fractions were concentrated under reduced pressure. The residue was recrystallized from a mixture of water and methanol (1 : 1 by volume) to give the objective compound (Ie) (680 mg). Yield, 78 %. m.p., 41°-42° C.

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