Next Article in Journal
3,8-Dihydroxy-2,9-dimethyl Deca-3,7-diene-5,6-dione
Previous Article in Journal
1-[5-Acetyl-4-(2-furyl)-2,6-dimethyl-1,4-dihydro-3-pyridinyl]-1-ethanone
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molbank
Volume 2002
Issue 1
10.3390/M281
molbank-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

(2Z)-3-(3,4-Dimethoxyphenyl)-2-(4-methylphenyl)acrylonitrile

by
Abdullah Mohamed Asiri
Chemistry Department, Faculty of Science, King Abdul-Aziz University, Jeddah 21589, P.O. Box 80203, Saudi Arabia
Molbank 2002, 2002(1), M281; https://doi.org/10.3390/M281
Submission received: 16 January 2002 / Revised: 15 March 2002 / Accepted: 15 May 2002 / Published: 16 February 2003
Versions Notes

Molbank 2002 m281 i001
(2Z)-3-(3,4-dimethoxyphenyl)-2-(4-methylphenyl)acrylonitrile (3) was prepared by Knoevenagel condensation of 3,4-dimethoxybenzaldehyde (1) and 4-methylphenylacetonitrile (2) in ethanol using KOH as a base [1,2]. 1 ( 1.31 g, 0.01 mol) and 2 (1.66 g, 0.01 mol ) in ethanol ( 25 mL) were heated under reflux for five minutes . Potassium hydroxide (0.56 g, 0.01 mol) was added in one portion and the reflux was continued for further two hours. The reaction mixture was cooled to room temperature and the solid formed was filtered, washed with water and finally with ethanol (2 x 20 mL) and dried. The product was recrystallized from ethanol as yellow crystals (2.63g, 95%).
M.p. 220-222 °C.
UV lmax (nm; EtOH)/e (dm3.mol-1.cm-1) 335/25000, 249/24500.
IR (cm-1; KBr Disk) 2207 (CN), 1615 (C=C).
1H-NMR (400 MHz; CDCl3, Me4Si, dH): 7.70 (1H, d, J= 2 Hz, H-2 ), 7.54 (2H, d, J= 8.2 Hz, H-2 ), 7.41 (1H, s, olefinic proton), 7.34 (1H, dd, J= 8.4, J 2 Hz, H-6), 7.24 (2H, d, J=8.03 Hz,), 6.91 (1H, d, J= 8.4 Hz), 3.96, 3.93 (6H, s, 2xMeO), 2.38 (3H, s, MePh).
13C-NMR (dC): 21.2, 55.95, 108.6, 110.5, 110.8, 118.8, 124.2, 125.6, 126.8, 129.7, 131.9, 138.9, 141.1, 148.9 and 150.9.
Elemental Analysis: Calculated for C18H17O2N (279.207): C 77.43%, H 6.09%, N 5.02%; Found: C 77.25%, H 4.96%, N 5.21%.

Supplementary Materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

  1. Jones, G. Org. React. 1967, 15, 204.
  2. Stewart, J. T.; Kim, M. J. Chem. Eng. Data 1987, 32, 387. [CrossRef]

Share and Cite

MDPI and ACS Style

Asiri, A.M. (2Z)-3-(3,4-Dimethoxyphenyl)-2-(4-methylphenyl)acrylonitrile. Molbank 2002, 2002, M281. https://doi.org/10.3390/M281

AMA Style

Asiri AM. (2Z)-3-(3,4-Dimethoxyphenyl)-2-(4-methylphenyl)acrylonitrile. Molbank. 2002; 2002(1):M281. https://doi.org/10.3390/M281

Chicago/Turabian Style

Asiri, Abdullah Mohamed. 2002. "(2Z)-3-(3,4-Dimethoxyphenyl)-2-(4-methylphenyl)acrylonitrile" Molbank 2002, no. 1: M281. https://doi.org/10.3390/M281

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

Article Metrics

Back to TopTop