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3':5'-diiodothyronine 30 minutes 5'-diiodothyronine acetic acid acetic anhydride acidification aldehyde alkali allowed to decompose amine hydrochloride amino acid Anal aqueous benzene bicarbonate solution Biochem boiling water Calcd casein Chem chloride cinnamic acid cooling crystals demethylation diiodotyrosine dilute alcohol dilute hydrochloric acid diphenyl ether linkage direct iodination dissolved ether group failure of thyronine filtered grams grams of iodine grams of sodium halogen Harington heated hydriodic acid hydrobromic acid hydrochloric acid hydrogen hypoiodous ice box overnight iodination of thyronine iodine atoms iodine content iodine monochloride isolated Lautemann's Red melting point method methyl mixture mols Mutzenbecher nitro compound OCH3 ortho oxidation p-hydroxybenzaldehyde p-hydroxybenzoic acid phenol phenolic ethers potassium carbonate potassium salt precipitate quinone recrystallized from alcohol rise to thyroxine sodium acetate sodium hydroxide solution soluble substance synthesis of thyroxine temperature thyroxine formation tion treated with iodine triiodophenol tyrosine washed water containing water was added yield of thyroxine