Next Article in Journal
Trimethyl 4-(4-Chlorophenyl)-2-hydroxy-2-(2-methoxy-2-oxoethyl)-6-oxo-1,3,5-cyclohexanetricarboxylate
Previous Article in Journal
(±)-2-tButyl-7-methoxy-1-oxaspiro[4,5]deca-6,9-diene-8-one
 
 
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

Trimethyl 2-Hydroxy-2-(2-methoxy-2-oxoethyl)-4-(4-methylphenyl)-6-oxo-1,3,5-cyclohexanetricarboxylate

Faculty of Pharmacy, Medical University of Sofia, Dunav 2, BG-1000 Sofia, Bulgaria
Molbank 2003, 2003(2), M323; https://doi.org/10.3390/M323
Submission received: 26 September 2002 / Accepted: 17 October 2002 / Published: 13 April 2003
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.
Molbank 2003 m323 i001
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 materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

  1. Haensel, W.; Haller, R. Arch. Pharm. (Weinheim Ger.) 1970, 303, 334–338.
  • Sample Availability: Available from the authors and from MDPI.

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

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

Article Metrics

Back to TopTop