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Short Note

(4-hydroxybenzylidene)-4-ferrocenylaniline

by
Ping Hu
,
Ke-Qing Zhao
* and
Hong-Bo Xu
Department of Chemistry, Sichuan Normal University, Chengdu, 610066, China
*
Author to whom correspondence should be addressed.
Molecules 2001, 6(12), M251; https://doi.org/10.3390/M251
Submission received: 28 May 2001 / Accepted: 14 December 2001 / Published: 20 December 2001
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes

Molecules 06 m251 i001
(4-Hydroxybenzylidene)-4-ferrocenylaniline has a free hydroxyl group and it can react with carboxylic acids to form esters and it is thus a key intermediate for the synthesis of mono-substituted ferrocene- containing liquid crystal [1] with Schiff's base and ester group. It can be synthesized by the condensation reaction of 4-ferrocenylaniline with 4-hydroxybenzaldehyde.
A stirred mixture of 4-ferrocenylaniline [2] (8.31g, 30mmol) and 4-hydroxybenzaldehyde(3.73 g, 30mmol) in 50 ml ethanol is heated under reflux for 2 h. The mixture is cooled and the precipitated product is collected by filtration as a yellow powder (10.5 g, 91%). The product is pure enough for analysis and for further use without further purification.
M.p: ca. 270°C (blackens and decomposes before melting).
IR(KBr, cm-1): 3465, 3070, 1645, 1584, 1530.
1HNMR (DMSO-d6, 300Hz): 10.11(1H, s, OH), 8.53(1H, S, CH=N), 4.02(5H, s, C5H5), 4.35-4.79(4H, d, C5H4), 6.88-7.80(4H, dd, J=9.0Hz, C6H4-OH), 7.16-7.56(4H, dd, J=8.9Hz, Fc-C6H4).
Elemental analysis for C23H19FeNO, calculated: C, 71.88; H, 4.95; N, 3.65%.
Found: C, 71.23; H, 4.84; N, 3.55%.

Supplementary Materials

References

  1. Espinet, P.; Esteruelas, M.A.; Oro, L.A.; Serrono, J.L.; Sola, E. Coor. Chem. Rev. 1992, 117, 215.
  2. Hu, P.; Zhao, K.-Q.; Xu, H.B. Molecules 2001, 6, M250.
Sample Availability: Available from the authors.

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MDPI and ACS Style

Hu, P.; Zhao, K.-Q.; Xu, H.-B. (4-hydroxybenzylidene)-4-ferrocenylaniline. Molecules 2001, 6, M251. https://doi.org/10.3390/M251

AMA Style

Hu P, Zhao K-Q, Xu H-B. (4-hydroxybenzylidene)-4-ferrocenylaniline. Molecules. 2001; 6(12):M251. https://doi.org/10.3390/M251

Chicago/Turabian Style

Hu, Ping, Ke-Qing Zhao, and Hong-Bo Xu. 2001. "(4-hydroxybenzylidene)-4-ferrocenylaniline" Molecules 6, no. 12: M251. https://doi.org/10.3390/M251

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