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Short Note

(4-Isopropenyl-cyclohex-1-enyl)acetic Acid Ethylester

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), M268; https://doi.org/10.3390/M268
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 m268 i001
The carbonylation of allylic componds catalyzed by transition metal complexes under atmospheric pressure of CO is one of the most attractive tools to synthesize the b ,g - unsaturated carbonyl compounds, which are versatile building blocks [1,2].
Pd(OAc)2 (7.5 mg, 0.033 mmol), anhydrous K2CO3 (135 mg, 9.7 moml) and a stirring bar were placed in a three necked flask. The atmosphere was replaced with carbon monoxide and 1-Chloromethyl-4-isopropenyl-cyclohexene, 1, [3] (3.3 mmol) in 5 ml of ethanol was added under CO. The reaction mixture was stirred at 25 °C for 1.5 hours. The reaction was followed by GC. At the end of the reaction, the mixture was filtered and the solvent was removed under vacuum. The residue was chromatographed on silica gel with Hexane / Ethyl acetate as eluent to provide the carbonylated product 2 [4] (Conversion: 100 %, Yield: 96 %).
[a]D20= -43.1° (c = 2.1; MeOH).
1H-NMR (300 MHz, CDCl3): 5.52 (1H, m, =CH); 4.66 (2H, m, =CH2); 4.1 (2H, q (J=7.1 Hz), OCH2CH3); 2.9 (2H, S, -CH2CO); 1.7 (3H, S, CH3); 1.2 (3H, t (J=7.1 Hz), OCH2CH3).
13C-NMR (100 MHz, CDCl3): 172 (C=O); 149.8 (=C); 130.9 (=C); 125.1 (=CH); 108.7 (=CH2); 60.5 (OCH2CH3); 43.2 (-CH2); 40.7 (-CH); 30.8 (-CH2); 28.9 (-CH2); 27.7 (-CH2); 20.8 (OCH2CH3); 14.3 (CH3).

References

  1. Tsuji, J.; Kiji, J.; Imanura, S.; Morikawa, M. J. Am. Chem. Soc. 1964, 86, 4350. [CrossRef]
  2. Kiji, J.; Okano, T.; Ono, I.; Komishi, H. J. Mol. Catal. 1987, 39, 355. [CrossRef]
  3. Barllargeon, V.P.; Still, J.K. J. Am. Chem. Soc. 1986, 108, 452.
  4. El Houssame, S.; El Firdoussi, L.; Allaoud, S.; Karim, A.; Castanet, Y.; Mortreux, A. J. Mol. Catal. 2001, 168, 15–23.
  • Sample Availability: Available from the authors and from MDPI.

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MDPI and ACS Style

El Houssame, S.; El Firdoussi, L.; Karim, A. (4-Isopropenyl-cyclohex-1-enyl)acetic Acid Ethylester. Molecules 2001, 6, M268. https://doi.org/10.3390/M268

AMA Style

El Houssame S, El Firdoussi L, Karim A. (4-Isopropenyl-cyclohex-1-enyl)acetic Acid Ethylester. Molecules. 2001; 6(12):M268. https://doi.org/10.3390/M268

Chicago/Turabian Style

El Houssame, Soufiane, Larbi El Firdoussi, and Abdellah Karim. 2001. "(4-Isopropenyl-cyclohex-1-enyl)acetic Acid Ethylester" Molecules 6, no. 12: M268. https://doi.org/10.3390/M268

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