2 research outputs found
Sintesis 2-((4-Alil-2-Metoksifenoksi)Metil)-5-(Metiltio)-1,3,4-Oxadiazola
No full textEugenol memiliki satu gugus aromatik yang mengandung substituen hidroksi (OH), alil (H2C=CH-CH2), dan metoksi (OCH3). Gugus hidroksi dan alil secara umum dimanfaatkan dalam modifiksi struktur eugenol untuk menghasilkan berbagai turunannya. Penelitian ini dilakukan untuk memperoleh turunan eugenol dengan substituen 1,3,4-oxadiazola berupa 2-((4-alil-2-metoksifenoksi)metil)-5-(metiltio)-1,3,4-oxadiazola . Sintesis senyawa dilakukan melalui reaksi substitusi gugus hidroksi eugenol oleh etil kloroasetat menghasilkan etil 2-(4-alil-2-metoksifenoksi)asetat dengan rendemen 93,53 %. Reaksi 2-(4-alil-2-metoksifenoksi)asetat selanjutnya dengan hidrazin hidrat memberikan 2-(4-alil-2-metoksifenoksi) asetohidrazida dengan rendemen 95,54 %. Pembentukan siklik 1,3,4-oxadiazola dilakukan antara 2-(4-alil-2-metoksifenoksi) asetohidrazida dengan karbon disulfida menghasilkan 5-((4-alil-2-metoksifenoki)metil)-1,3,4-oxadiazola-2-tiol dengan rendemen 25,27 %. Selanjutnya, metilasi 5-((4-alil-2-metoksifenoki)metil)-1,3,4-oxadiazola-2-tiol oleh metil iodida memberikan 2-((4-alil-2-metoksifenoksi)metil)-5-(metiltio)-1,3,4-oxadiazola dengan rendemen 95,75 %.
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Eugenol has an aromatic group containing hydroxy (OH), allyl (H2C=CH-CH2), and methoxy (OCH3) substituents. Hydroxy and allyl groups are generally used in the modification of the eugenol structure to produce various derivatives. This research was conducted to obtain a eugenol derivative with a 1,3,4-oxadiazole substituent in the form of 2-((4-allyl-2-methoxyphenoxy)methyl)-5-(methyltio)-1,3,4-oxadiazola. The synthesis of the compound was carried out through the substitution reaction of the hydroxy eugenol group by ethyl chloroacetate to produce ethyl 2-(4-allyl-2-methoxyphenoxy) acetate with a yield of 93,53 %. Further reaction of 2-(4-allyl-2-methoxyphenoxy) acetate with hydrazine hydrate gave 2-(4-allyl-2-methoxyphenoxy)acetohydrazide with a yield of 95,54 %. Cyclic formation of 1,3,4-oxadiazola is carried out between 2-(4-allyl-2-ethoxyphenoxy)acetohydrazide with carbon disulfide to produce 5-((4-allyl-2-methoxyphenoxy) methyl)-1,3,4-oxadiazola- 2-thiol with a yield of 25.27%.
Furthermore, the methylation of 5-((4-allyl-2-methoxyphenoxy) methyl)-1,3,4-oxadiazola-2-thiol by methyl iodide gives 2-((4-allyl-2-methoxyphenoxy)methyl)-5-(methyltio)-1,3,4-oxadiazola with yield of 95,75 %
Modifikasi Struktur Eugenol Menjadi Etil 2-(4-Alil-2-Metoksifenoksi) Asetat Melalui Reaksi Alkilasi dengan Etil Kloroasetat
No full textEugenol, a natural product with broad and promising biological activity, possesses three reactive functional groups of hydroxyl, allyl, and methoxy, which can be transformed through chemical reactions into various derivatives. The reaction of eugenol and ethyl chloroacetate with a mole ratio of 1:1 has been reported to produce an alkylation product. However, the use of dry acetone as a solvent and the reflux condition for 12 hours were the drawbacks of this reaction. The structural modification of eugenol into ethyl 2-(4-allyl-2methoxyphenoxy) acetate as an alkylation product was further studied in this paper. The alkylation reaction of eugenol and ethyl chloroacetate was performed in dimethylformamide with a mole ratio of 6:10 (method A), 1:1 (method B), 1:4 (method C), and 1:4 (method D) at room temperature (methods A and D) and under reflux conditions (methods B and C). The results showed that the alkylation reaction with a mole ratio of 1:4 at room temperature (method D) produced ethyl 2-(4-allyl-2-methoxyphenoxy)acetate as a pure compound with a yield of 94%. The structure of the alkylation product was determined by FTIR, NMR spectroscopy, and mass analysis. Ethyl 2-(4-allyl-2-methoxyphenoxy)acetate is a key compound in the development of various eugenol-derived active compounds
