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Short Note

(E)-3-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), M53; https://doi.org/10.3390/M53
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 m53 i001
The general part of the experimental section [1] has been presented elsewhere. Ethyl (E)-3-methyl-
5-phenyl-2-pentenoate (3.363 g, 15.4 mmol) was refluxed with sodium hydroxide (2.161 g, 38.5 mmol) in a mixture of water (50 ml) and methanol (10 ml) for 3 hours, cooled and washed with ether (30 ml). The aqueous phase was acidified with concentrated hydrochloric acid to below pH 1. The mixture was extracted with ether (3x30 ml). The combined ether extracts were washed with brine (20 ml), dried (Na2SO4), filtered and evaporated under reduced pressure. (E)-3-Methyl-5-phenyl-2-pentenoic acid (2.79 g, 95%) was obtained as colourless plates from cyclohexane/light petroleum.
M.p. 58°
Anal. calc. for C12H14O2 (190.24): C 75.8, H 7.4; found: C 76.2, H 7.3.
UV (ethanol) 305 (208) nm.
IR (CDCl3) 3500–2800(bs, OH), 3104, 2950, 1694 (s, C=O), 1641, 1260 cm−1.
1H-NMR (90 MHz, CDCl3) 2.16 (3H, d, J 1.1 Hz, CH3), 2.43 (2H, m, =C(CH2), 2.73 (2H, m, Ph-CH2),
5.61 (1H, m, =CH), 6.92–7.40 (5H, m, ArH), 9.98 (1H, bs, COOH).
13C-NMR (15 MHz, CDCl3) 19.22 (CH3), 34.02, 42.85 (CH2), 115.7 (=CH); 126.2, 128.2 128.5 (ArCH),
140.9 (quat, C1’), 161.7 (quat, C3), 171.5 (quat, C1).
EI-MS 190(M+, 3%), 144(10), 91(100).

Supplementary Materials

Acknowledgments

The authors gratefully acknowledge financial support from the Australian Research Council and The University of Sydney.

Reference

  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)-3-Methyl-5-phenyl-2-pentenoic Acid. Molecules 1998, 3, M53. https://doi.org/10.3390/M53

AMA Style

Stoermer MJ, Pinhey JT. (E)-3-Methyl-5-phenyl-2-pentenoic Acid. Molecules. 1998; 3(3):M53. https://doi.org/10.3390/M53

Chicago/Turabian Style

Stoermer, Martin J., and John T. Pinhey. 1998. "(E)-3-Methyl-5-phenyl-2-pentenoic Acid" Molecules 3, no. 3: M53. https://doi.org/10.3390/M53

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