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• W2080854898 abstract "first_page settings Order Article Reprints Font Type: Arial Georgia Verdana Font Size: Aa Aa Aa Line Spacing:    Column Width:    Background: Open AccessShort Note Trimethyl 2-Hydroxy-2-(2-methoxy-2-oxoethyl)-4-(4-methylphenyl)-6-oxo-1,3,5-cyclohexanetricarboxylate by Edmont V. Stoyanov Faculty of Pharmacy, Medical University of Sofia, Dunav 2, BG-1000 Sofia, Bulgaria Molbank 2003, 2003(2), M323; https://doi.org/10.3390/M323 Received: 26 September 2002 / Accepted: 17 October 2002 / Published: 13 April 2003 Download Download PDF Download PDF with Cover Download XML Download Epub Download Supplementary Material Versions Notes Keywords: Michael addition; cyclohexanone; dimethyl acetonedicarboxylate; cyclization Aromatic aldehydes react with dimethyl acetonedicarboxylate in molar ratio 1:2 with spontaneous intermolecular Michael addition to give polysubstituted cyclohexanones [1]. We report now the synthesis of an analogous product from 4-methylbenzaldehyde.To a solution of 4-methylbenzaldehyde (1.20 g, 10 mmol) and dimethyl acetonedicarboxylate (3.48 g, 20 mmol) in 25 ml ethanol, 0.3 ml piperidine was added. The reaction mixture was left to stay at room temperature for 3 days. The separated crystals were filtered off, washed with cold ethanol, recrystallized from dioxane and air-dried. Yield: 3.18 g (71 %).Colorless crystals, m. p. 149-150 °C (dec.) from dioxane.1H NMR (300 MHz, d6-DMSO): 2.23 (s, 3H, PhCH3), 2.43 (d, 1H, J=17.0 Hz, HCH), 2.96 (d, 1H, J=17.0 Hz, HCH), 3.44 (s, 3H, OCH3), 3.52 (d, 1H, J=12.2 Hz, H-3), 3.56 (s, 3H, OCH3), 3.60 (s, 3H, OCH3), 3.66 (s, 3H, OCH3), 3.94 (t, J1=J2=12.2 Hz, H-4), 4.38 (d, 1H, J=12.2 Hz, H-5), 4.67 (s, 1H, H-1), 5.40 (s, 1H, OH), 7.06 (d, 2H, J=8.0 Hz, 2' and 6'H arom.), 7.19 (d, 2H, J=8.0 Hz, 3' and 5'H arom.).13C NMR (75 MHz, d6-DMSO): 41.4, 42.8, 51.1, 51.5, 51.6, 51.7, 54.3, 61.2, 62.8, 66.3, 74.3, 128.1 (2xC), 128.9 (2xC), 136.2, 136.6 (2xC), 167.7, 168.2, 169.5, 169.8.FT IR (KBr, cm-1): 3511, 2953, 1729, 1516, 1495, 1364.ESI MS [FIA in MeOH, CH3COONH4/CH3COOK]: 468.2 [M+NH4]+, 489.2 [M+K]+. Supplementary materialsSupplementary File 1Supplementary File 2Supplementary File 3ReferencesHaensel, W.; Haller, R. Arch. Pharm. (Weinheim Ger.) 1970, 303, 334–338.Sample Availability: Available from the authors and from MDPI. © 2003 MDPI. All rights reserved. Share and Cite MDPI and ACS Style Stoyanov, E.V. Trimethyl 2-Hydroxy-2-(2-methoxy-2-oxoethyl)-4-(4-methylphenyl)-6-oxo-1,3,5-cyclohexanetricarboxylate. Molbank 2003, 2003, M323. https://doi.org/10.3390/M323 AMA Style Stoyanov EV. Trimethyl 2-Hydroxy-2-(2-methoxy-2-oxoethyl)-4-(4-methylphenyl)-6-oxo-1,3,5-cyclohexanetricarboxylate. Molbank. 2003; 2003(2):M323. https://doi.org/10.3390/M323 Chicago/Turabian Style Stoyanov, Edmont V. 2003. Trimethyl 2-Hydroxy-2-(2-methoxy-2-oxoethyl)-4-(4-methylphenyl)-6-oxo-1,3,5-cyclohexanetricarboxylate Molbank 2003, no. 2: M323. https://doi.org/10.3390/M323 Find Other Styles Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here. Article Metrics No No Article Access Statistics For more information on the journal statistics, click here. Multiple requests from the same IP address are counted as one view." @default.
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• W2080854898 title "Trimethyl 2-Hydroxy-2-(2-methoxy-2-oxoethyl)-4-(4-methylphenyl)-6-oxo-1,3,5-cyclohexanetricarboxylate" @default.
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