SYNTHESIS OF SOME CINNAMIC ACID DERIVATIVES: EFFECT OF GROUPS ATTACHED ON AROMATIC RING TO THE REACTIVITY OF BENZALDEHYDE

https://doi.org/10.22146/ijc.21626

Marcellino Rudyanto(1*), Lanny Hartanti(2)

(1) Research and Community Service Institute, Widya Mandala Catholic University, Jl. Dinoyo 42-44 Surabaya 60265
(2) Faculty of Pharmacy, Widya Mandala Catholic University, Jl. Dinoyo 42-44 Surabaya 60265
(*) Corresponding Author

Abstract


Synthesis of cinnamic acid and its six derivatives has been done by employing Knoevenagel reaction. Benzaldehyde, 4-butylbenzaldehyde, 4-t-butylbenzaldehyde, 4-butoxybenzaldehyde, 4-phenylbenzaldehyde, 5-bromo-2,4-dimethoxybenzaldehyde, and 5-bromo-2,3-dimethoxybenzaldehyde were reacted with malonic acid in pyridine – piperidine to give cinnamic acid (85,3%), 4-butylcinnamic acid (69,3%), 4-t-butylcinnamic acid (77,7%), 4-butoxycinnamic acid (64,5%), 4-phenylcinnamic acid (65,5%), 5-bromo-2,4-dimethoxycinnamic acid (53,2%) and 5-bromo-2,4-dimethoxycinnamic acid (57,2%), respectively. It was disclosed that 4-alkyl, 4-alkoxy, 4-aryl, dan 2-alkoxy groups decrease the reactivity of carbonyl carbon of benzaldehyde.


Keywords


cinnamic acid; cinnamic acid derivatives; Knoevenagel reaction

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DOI: https://doi.org/10.22146/ijc.21626

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