Next Article in Journal
4,5-Dimethoxy-2-nitrobenzophenone
Previous Article in Journal
N-(3-Phenyl-2-propinoyl)benzamide
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molecules
Volume 4
Issue 10
10.3390/M109
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

4-[5-(4-methylphenyl)-2-furfuryl]iden-2-butenolide

by
Lyudmila N. Sorotskaya
1,
Larisa A. Badovskaya
2,
Tatyana Ya. Kaklyuginac
3 and
Aryan Younessi
1
1
Laboratory of Furan Chemistry, Kuban State Technological University, Moskovskaya st. 2, Krasnodar 350072, Russia
2
Department of General Chemistry, Kuban State Technological University, Moskovskaya st. 2, Krasnodar 350072, Russia
3
Department of Organic Chemistry, Kuban State Technological University, Moskovskaya st. 2, Krasnodar 350072, Russia
Molecules 1999, 4(10), M109; https://doi.org/10.3390/M109
Submission received: 25 August 1999 / Accepted: 8 September 1999 / Published: 8 October 1999
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 04 m109 i001
The general part of the experimental section [1] has been presented elsewhere. 2-Butenolide (7.6 ml, 0.1 mol) and piperidine (2.5 ml, 0.025 mol) were dissolved in ethanol (50 ml), and then under stirring a solution of 5-(4-methyl-phenyl)furfural (9.3 g, 0.05 mol) in 50 ml of ethanol was added to this mixture. The reaction mixture was left to stand at the room temperature for three days until the initial aldehyde was consumed (control TLC). After that the reaction mixture was cooled to crystallize the desired product. The obtained crystals were filtered off and recrystallized from ethanol giving 11.3 g (90 %) of 4-[5-(4-methylphenyl)-2-furfuryl]iden-2-butenolide.
M.p. 147-148°C (ethanol).
UV (EtOH) [λmax (nm), log ε (dm3mol-1cm-1)]: 275 (3.92), 420 (4.12).
IR (cm-1): 1640 (C=C); 1750 (C=O), 1780 (C=O).
1H NMR (CDCl3, 250 MHz): 7.65 (d, 2H, o-HAr, J = 8.4 Hz); 7.60 (d, 2H, m-HAr, J = 8.4 Hz); 7.49 (d, 1H, HB, JBA = 5.2 Hz); 7.15 (d, 1H, HD, JDE = 3.5 Hz); 6.78 (d, 1H, HE, JED = 3.5 Hz); 6.18 (dd, 1H, HA, JAB = 5.2 Hz, JAC = 0.8 Hz); 6.13 (br s, 1H, HC, JCA = 0.8 Hz); 2.38 (s, 3H, CH3).
EI-MS: 252 (M+ 100%); 224 (17%).
Anal. calc. for C16H12O3 (252.26): C 76.15, H 4.80; Found C 75.89, H 4.70.

Supplementary materials

Supplementary File 1Supplementary File 2

Reference

  1. Sorotskaya, L.N.; Badovskaya, L.A.; Kaklyugina, T.Y.; Belen'kij, L.I.; Ignatenko, A.V.; Krutoshikova, A.; Panieva, L.A. Zhurnal Organich. Khimii (Journal of Organic Chemistry - Russian Edition) 1989, 25, 175.
  • Sample availability: available from authors (Dr. Lyudmila N. Sorotskaya) and MDPI.

Share and Cite

MDPI and ACS Style

Sorotskaya, L.N.; Badovskaya, L.A.; Kaklyuginac, T.Y.; Younessi, A. 4-[5-(4-methylphenyl)-2-furfuryl]iden-2-butenolide. Molecules 1999, 4, M109. https://doi.org/10.3390/M109

AMA Style

Sorotskaya LN, Badovskaya LA, Kaklyuginac TY, Younessi A. 4-[5-(4-methylphenyl)-2-furfuryl]iden-2-butenolide. Molecules. 1999; 4(10):M109. https://doi.org/10.3390/M109

Chicago/Turabian Style

Sorotskaya, Lyudmila N., Larisa A. Badovskaya, Tatyana Ya. Kaklyuginac, and Aryan Younessi. 1999. "4-[5-(4-methylphenyl)-2-furfuryl]iden-2-butenolide" Molecules 4, no. 10: M109. https://doi.org/10.3390/M109

Article Metrics

Back to TopTop