The Preparation of Aromatic Alcohols by the Crossed Cannizzaro Reaction with Formaldehyde

Abstract

Aromatic Alcohols by the Crossed Cannizzaro Reaction 905 When the azide was taken up in ether, a sparingly soluble by-product separated crystalline from benzene, m. p. 220-222°. A second by-product (140-160°) is found in the crude oily urethan. (4) The urethan yields 96% of 2-[ -amino-M-propylJ-dibenzofuran hydrochloride, m. p. 228-231°, corr. (M. and K" 219-220°).One gram of 2-[7-amino-re-propyl ]-dibenzofuran hydrochloride, 1 g. of 99-100% formic acid, and 10 g. of 37% aqueous formaldehyde were heated in a sealed tube for fifteen hours at 130-160°. After treatment of the basic reaction products with benzene sulfonyl chloride, 0.45 g. of the hydrochloride of 2-[ 7-(dimethylamino)-re-propyl ]dibenzofuran, m. p. 190-193°was obtained, and purified by repeated crystallization. Summary 1. The synthesis of benzofuro-[3,2-g]-quinoline and benzofuro-[2,3-f ]-quinoline from 3-aminodibenzofuran is described.2. The tetrahydro and N-methyltetrahydro compounds of the benzofuroquinolines were prepared.3. The constitution of the benzofuro-quinolines has been proved through the Emde degradation products of the N-methyltetrahydrobenzofuro-quinolines. University, Virginia

Organic reactions for the electrochemical and photochemical production of chemical fuels from CO2 – The reduction chemistry of carboxylic acids and derivatives as bent CO2 surrogates

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“…Enolizable aldehydes react with formaldehyde in strong aqueous base to form polyols, whereas ketones usually react to form polyhydroxyketones (Davidson & Bogert, 1935;Vik et al, 1973;Weissermel & Arpe, 1997;Wittcoff et al, 2013). Therefore, the observed methylation of 9-acetylanthracene by formaldehyde with alcoholic potassium carbonate (see Scheme below) is remarkable in that the reaction occurs with weak base in a non-aqueous medium by reduction of formaldehyde to form the methyl group (Pande et al, 1998).…”

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