Next Article in Journal
(4-Isopropenyl-cyclohex-1-enyl)acetic Acid Ethylester
Previous Article in Journal
3,5-Bis(trimethylsilyl)-4-thiophenoxypyridine
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molecules
Volume 6
Issue 12
10.3390/M267
molecules-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

3-(4’-Methyl-3’-oxocyclohex-1’-enyl)butyric Acid Methyl Ester

by
Soufiane El Houssame
*,
Larbi El Firdoussi
and
Abdellah Karim
Laboratoire de Chimie de Coordination, Faculté des Sciences Semlalia, BP 2390 Marrakech Morocco
*
Author to whom correspondence should be addressed.
Molecules 2001, 6(12), M267; https://doi.org/10.3390/M267
Submission received: 14 June 2001 / Accepted: 15 December 2001 / Published: 20 December 2001
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 06 m267 i001
The alkoxycarbonylation of terpenic olefins which affords the corresponding esters is an elegant synthesis [1-2]. Morover, the metal-complex-catalyzed hydrocarboxylation is among the most extensively investigated processes in homogeneous catalysis[3].
In a flask fitted with a reflux condenser was placed PdCl2 (34 mg, 0.19 mmol), Cu(OAc)2 (1.1 g, 5.5 mmol) and p-Toluenesulfonic acid (PTSA) (69.6 mg, 0.36 mmol), and the atmosphere was replaced with CO/O2 (1:1). 15 ml of methanol were added and the mixture was stirred for 15 min at room temperature under atmospheric pressure of CO/O2. 3-Isopropenyl-6-methyl-cyclohexene, 1, (3.6 mmol ) prepared by pyrolysis of 2-carene at high temperature (>220 °C) was added. The resulting mixture was further stirred at room temperature and at CO/O2 was bubbled in for 5 days. The reaction was monitored by GC (conversion = 94%).
At the end of the reaction, the solvent was removed by rotary evaporation. The residue was purified by using silica gel chromatography column with Hexane/AcOEt (96:4) to afford 2 as colorless oil (46%).
1H-NMR (300 MHz, CDCl3): 5.72 (1H, dd, J1=3.26 Hz/J2=1.31Hz); 3.6 (3H, S, O-CH3); 1.07 (3H, d, J=7.18 Hz, CH3); 1.01(3H, d, J=6.53 Hz, CH3).
13C-NMR (100 MHz, CDCl3): 202.2 (C=O); 172.1 (C=O); 167.4 (=C); 124 (=CH); 51.6 (OCH3); 40.9 (-CH); 39.3 (-CH2); 37.5 (-CH); 30.7 (-CH2); 27.1 (CH2); 19 (CH3); 14.9 (CH3).
M.S: m/z 210 (M+); 151 (59); 109 (42).

Supplementary Material

References

  1. Naigre, R.; Chenal, T.; Ciprès, I.; Kalck, P.; Daran, J.C.; Vaissermann, J. J. Org. Chem. 1994, 480, 91–102. [CrossRef]
  2. Chenal, T.; Ciprès, I.; Jenck, J.; Kalck, P.; Peres, Y. J. Mol .Catal. 1993, 78, 351–366. [CrossRef]
  3. Tkatchenko, I. Comprehensive Organometallic Chemistry; Vol. 8, Pergamon, Oxford, (1982); pp. 101–223. [Google Scholar]
Sample Availability: Available from the authors and from MDPI.

Share and Cite

MDPI and ACS Style

El Houssame, S.; El Firdoussi, L.; Karim, A. 3-(4’-Methyl-3’-oxocyclohex-1’-enyl)butyric Acid Methyl Ester. Molecules 2001, 6, M267. https://doi.org/10.3390/M267

AMA Style

El Houssame S, El Firdoussi L, Karim A. 3-(4’-Methyl-3’-oxocyclohex-1’-enyl)butyric Acid Methyl Ester. Molecules. 2001; 6(12):M267. https://doi.org/10.3390/M267

Chicago/Turabian Style

El Houssame, Soufiane, Larbi El Firdoussi, and Abdellah Karim. 2001. "3-(4’-Methyl-3’-oxocyclohex-1’-enyl)butyric Acid Methyl Ester" Molecules 6, no. 12: M267. https://doi.org/10.3390/M267

Article Metrics

Back to TopTop