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Majalah Farmasi Airlangga (Airlangga Journal of Pharmacy)

ISSN 0852-1050

Vol. 5 / No. 3 / Published : 2005-12

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Original Article :

Pengaruh posisi gugus metoksi para dan meta terhadap hasil sintesis asam para-metoksisinamat dan asam meta-metoksisinamat

Author :

  1. Juni Ekowati*1
  2. Suzana*2
  3. Tutuk Budiati*3
  1. Bagian Kimia Farmasi, Fakultas Farmasi Universitas Airlangga
  2. Bagian Kimia Farmasi, Fakultas Farmasi Universitas Airlangga
  3. Bagian Kimia Farmasi, Fakultas Farmasi Universitas Airlangga

Abstract :

The effect of position of methoxy group on synthesis of m-methoxycinnamic acid and p-methoxycinnamic acid through Knoevenagel reaction had been carried out. The synthesis was carried out by reacting the p-methoxybenzaldehyde and m-methoxybenzaldehyde with malonic acid in the present of pyridine. The mixture was stirred at 80C and monitored by TLC (hexane: ethyl acetate; 4:2;5 h), on silica gel (60 F254;0,2 mm). The m-methoxycinnamic acid (70%, m.p. 112oC), p-methoxycinnamic acid (54%, m.p. 170oC) were obtained as colourless crystal. The results showed that methoxy group at para position could decrease the Knoevenagel reaction because of steric effect and gave [+ M] effect, which could complicate nucleophylic addition in Knoevenagel reaction. On the other hand, methoxy group at meta position will give [-I] effect that enhanced the Knoevenagel reaction.

Keyword :

Knoevenagel reaction, [+M] effect, [-I] effect, methoxy group, synthesis, m-methoxycinnamic acid, p-methoxycinnamic acid,


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Archive Article

Cover Media Content

Volume : 5 / No. : 3 / Pub. : 2008-01
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