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Short Note

(E)-2-Methyl-5-phenyl-2-pentenoic Acid

by
Martin J. Stoermer
* and
John T. Pinhey
Division of Organic Chemistry, School of Chemistry F11, The University of Sydney, N.S.W 2006, Australia
*
Author to whom correspondence should be addressed.
*
Current address: Victorian College of Pharmacy, Monash University (Parkville Campus), 381 Royal Parade, Parkville, Victoria 3052, Australia
Molecules 1998, 3(3), M64; https://doi.org/10.3390/M64
Submission received: 27 February 1998 / Published: 6 March 1998
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 03 m64 i001
The general part of the experimental section [1] has been presented elsewhere. Ethyl (E)-2-methyl-5-phenyl-2-pentenoate (2.345 g, 10.7 mmol) was refluxed with potassium hydroxide (1.55 g, 27.6 mmol) in a mixture of water (80 ml) and methanol (10 ml) for 3 hours, cooled and washed with ether (50 ml). The aqueous phase was acidified with concentrated hydrochloric acid to below pH 1. The mixture was extracted with ether (3x50 ml). The combined ether extracts were washed with brine (20 ml), dried (Na2SO4), filtered and evaporated under reduced pressure. (E)-2-Methyl-5-phenyl-2-pentenoic acid (1.71 g, 84%) was obtained as a viscous pale yellow oil that crystallized on standing at room temperature overnight.
M.p. 36-7°
Anal. calc. for C12H14O2 (190.24): C 75.8, H 7.4; found: C 75.5, H 7.6.
IR (CDCl3) 3500-2800(bs, OH), 3027, 2930(s), 2670(s), 1685 (s, C=O), 1642, 1422, 1286(s), 933, 739, 698 cm-1.
1H-NMR (90 MHz, CDCl3) 1.75 (3H, bs, CH3), 2.23-2.90 (4H, m, 2xCH2), 6.87 (1H, tq, J 7.5, 1.5 Hz, =CH), 6.70-7.37 (5H, m, ArH), 11.50 (1H, bs, COOH).
13C-NMR (15 MHz, CDCl3) 11.69 (CH3), 30.52, 34.41 (CH2), 126.0 (ArCH), 127.8 (quat, C2), 128.2 128.3 (ArCH), 140.9 (quat, C1'), 143.5 (=CH); 173.5 (quat, C1).
EI-MS 190(M+, 10%), 91(100), 44(89).
Acknowledgment: The authors gratefully acknowledge financial support from the Australian Research Council and The University of Sydney.

References and Notes

  1. Moloney, M.G.; Pinhey, J.T.; Stoermer, M.J. "Vinyl Cation Formation by Decomposition of Vinyl-lead Triacetates. The reactions of Vinylmercury and Vinyltin Compounds with Lead Tetraacetate". J. Chem. Soc. Perkin Trans. 1 1990, 10, 2645. [Google Scholar] [CrossRef]
Sample Availability: No sample available.

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MDPI and ACS Style

Stoermer, M.J.; Pinhey, J.T. (E)-2-Methyl-5-phenyl-2-pentenoic Acid. Molecules 1998, 3, M64. https://doi.org/10.3390/M64

AMA Style

Stoermer MJ, Pinhey JT. (E)-2-Methyl-5-phenyl-2-pentenoic Acid. Molecules. 1998; 3(3):M64. https://doi.org/10.3390/M64

Chicago/Turabian Style

Stoermer, Martin J., and John T. Pinhey. 1998. "(E)-2-Methyl-5-phenyl-2-pentenoic Acid" Molecules 3, no. 3: M64. https://doi.org/10.3390/M64

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