Next Article in Journal
Ethyl (E)-2-Methyl-5-phenyl-2-pentenoate
Previous Article in Journal
Ethyl 3-Acetoxy-3-methyl-5-phenylpentanoate
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molecules
Volume 3
Issue 3
10.3390/M61
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-Hydroxy-3-methyl-5-phenylpentanoic 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), M61; https://doi.org/10.3390/M61
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 m61 i001
The general part of the experimental section [1] has been presented elsewhere. Ethyl 3-hydroxy-3-methyl- 5-phenylpentanoate (1.00 g, 4 mmol) and potassium hydroxide (0.6 g, 11 mmol) in water (20 ml) and methanol (4 ml) were refluxed for 3 hours, cooled and washed with ether (20 ml). The aqueous phase was acidified with concentrated hydrochloric acid to below pH 1 and extracted with ether (3x20 ml). The combined ether extracts were dried (Na2SO4), filtered and evaporated under reduced pressure to yield 3-hydroxy-3-methyl-5-phenylpentanoic acid.
(0.57 g, 65%).
M.p. 45°
UV (ethanol) 295 (83), 268 (223), 261 (285), 255sh (250), 249 (202) nm.
IR (CDCl3) 3500-2800(bs, OH), 3029, 2982, 1707 (s, C=O), 704 cm-1.
1H-NMR (90 MHz, CDCl3) 1.33 (3H, s, CH3), 1.83 (2H, m, CH2), 2.55 (2H, s, CH2), 2.68 (2H, s, Ph-CH2), 6.92 (2H, bs, 2xOH), 7.12 (5H, m, ArH).
13C-NMR (15 MHz, CDCl3) 26.56 (CH3), 30.19, 43.63, 44.74 (CH2), 71.36 (quat, C3), 125.8, 128.2
128.4 (ArCH), 141.8 (quat, C1'), 177.1 (quat, C1).
EI-MS 190(M+-H2O, 31%), 131(63), 105(25), 103(18), 91(100), 85(12).
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.

Share and Cite

MDPI and ACS Style

Stoermer, M.J.; Pinhey, J.T. 3-Hydroxy-3-methyl-5-phenylpentanoic Acid. Molecules 1998, 3, M61. https://doi.org/10.3390/M61

AMA Style

Stoermer MJ, Pinhey JT. 3-Hydroxy-3-methyl-5-phenylpentanoic Acid. Molecules. 1998; 3(3):M61. https://doi.org/10.3390/M61

Chicago/Turabian Style

Stoermer, Martin J., and John T. Pinhey. 1998. "3-Hydroxy-3-methyl-5-phenylpentanoic Acid" Molecules 3, no. 3: M61. https://doi.org/10.3390/M61

Article Metrics

Back to TopTop