4,5-Dimethoxy-2-nitrobenzhydrol
Sergey K. Smirnov, Tat'yana A. Stroganova and Alexander V. Butin
Reasearch Laboratory of Furan Chemistry, Kuban State Technological University, Moskovskaya 2, Krasnodar, Russian Federation. Phone: +7 8612 55 95 56; E-mail: [email protected], E-mail: [email protected]
Received: 13 September 1999 / Accepted: 20 September 1999 / Published: 8 October 1999
The general part of the experimental section [1] has been presented elsewhere. To a boiling solution of 4,5-dimethoxy-4-nitrobenzophenone (10.0 g, 35 mmol) in ethanol (85 ml), NaBH4 (0.61 g) was added gradually. After an hour the reaction mixture was diluted with water (300 ml) and then acidified with hydrochloric acid (20 %) to pH 6. The precipitate obtained was filtered off and recrystallized from ethanol to yield 7.75 g (77 %) of 4,5-dimethoxy-2-nitrobenzhydrol as yellow needles.
M.p. 130¡ãC (ethanol).
IR (cm-1): 3500 (OH).
1H NMR (CDCl3, 80 MHz): 7.47 (s, 1H,3-HAr); 7.17 (s, 5H, HPh); 7.13 (s, 1H, 6-HAr); 6.37 (s, 1H, CH); 3.80 (s, 6H, OCH3); 3.12 (broad s, 1H, OH).
Anal. calc. for C15H15NO5 (289.30): C 62.28, H 5.23; Found: C 62.03, H 5.41.
Reference
1. Gutnov, A.V.; Butin, A.V.; Abaev, V.T.; Krapivin, G.D.; Zavodnik, V.E. Furyl(aryl)alkanes and Their Derivatives.19. Synthesis of Benzofuran Derivatives via 2-Hydroxyaryl-R-(5-methylfur-2-yl)methanes. Reaction of Furan Ring Opening - Benzofuran Ring. Molecules 1999, 4, 204-218.
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