Next Article in Journal
5-(1-Acetamido)benzyl-5-methyl Imidazolidin-2,4-dione
Previous Article in Journal
Trimethyl 2-Hydroxy-2-(2-methoxy-2-oxoethyl)-4-(4-methylphenyl)-6-oxo-1,3,5-cyclohexanetricarboxylate
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molbank
Volume 2003
Issue 2
10.3390/M324
molbank-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles thumb_up
...
Endorse textsms
...
Comment
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

Trimethyl 4-(4-Chlorophenyl)-2-hydroxy-2-(2-methoxy-2-oxoethyl)-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), M324; https://doi.org/10.3390/M324
Submission received: 26 September 2002 / Accepted: 17 October 2002 / Published: 13 April 2003
Versions Notes

Aromatic aldehydes react with dimethyl acetonedicarboxylate in molar ratio 1:2 with spontaneous intramolecular Michael addition to give polysubstituted cyclohexanones [1]. We report now the synthesis of an analogous product from 4-chlorobenzaldehyde.
Molbank 2003 m324 i001
To a solution of 4-chlorobenzaldehyde (1.41 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: 2.93 g (62 %).
Colorless crystals, m. p. 159-160 °C (dec.) from dioxane.
1H NMR (300 MHz, d6-DMSO): 2.44 (d, 1H, J=17.1 Hz, HCH), 2.98 (d, 1H, J=17.1 Hz, HCH), 3.34 (s, 3H, OCH3), 3.47 (s, 3H, OCH3), 3.56 (d, 1H, J=12.2 Hz, H-3), 3.58 (s, 3H, OCH3), 3.67 (s, 3H, OCH3), 3.98 (t, 1H, J1=J2=12.2 Hz, H-4), 4.44 (d, 1H, J=12.2 Hz, H-5), 4.69 (s, 1H, H-1), 5.51 (s, 1H, OH), 7.20-7.36 (m, 4H arom.).
13C NMR (75 Hz, d6-DMSO): 41.3, 42.6, 51.2, 51.5, 51.7 (2xC), 54.1 (2xC), 60.8, 62.8, 74.3, 128.3 (2xC), 130.2 (2xC), 138.6, 167.5, 168.0, 169.4, 169.6.
FT IR (KBr, cm-1): 3503, 2958, 1732, 1495, 1436, 1350, 1310.
ESI MS [FIA in MeOH, CH3COONH4/CH3COOK]: 509.2 [M+K]+, 453 [M-H2O]+.

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 4-(4-Chlorophenyl)-2-hydroxy-2-(2-methoxy-2-oxoethyl)-6-oxo-1,3,5-cyclohexanetricarboxylate. Molbank 2003, 2003, M324. https://doi.org/10.3390/M324

AMA Style

Stoyanov EV. Trimethyl 4-(4-Chlorophenyl)-2-hydroxy-2-(2-methoxy-2-oxoethyl)-6-oxo-1,3,5-cyclohexanetricarboxylate. Molbank. 2003; 2003(2):M324. https://doi.org/10.3390/M324

Chicago/Turabian Style

Stoyanov, Edmont V. 2003. "Trimethyl 4-(4-Chlorophenyl)-2-hydroxy-2-(2-methoxy-2-oxoethyl)-6-oxo-1,3,5-cyclohexanetricarboxylate" Molbank 2003, no. 2: M324. https://doi.org/10.3390/M324

APA Style

Stoyanov, E. V. (2003). Trimethyl 4-(4-Chlorophenyl)-2-hydroxy-2-(2-methoxy-2-oxoethyl)-6-oxo-1,3,5-cyclohexanetricarboxylate. Molbank, 2003(2), M324. https://doi.org/10.3390/M324

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