Sintesis 2-((4-Alil-2-Metoksifenoksi)Metil)-5-(Metiltio)-1,3,4-Oxadiazola

Agistya, Hamida Azza (2023) Sintesis 2-((4-Alil-2-Metoksifenoksi)Metil)-5-(Metiltio)-1,3,4-Oxadiazola. Other thesis, Institut Teknologi Sepuluh Nopember.

Text 01211940000095-Undergraduate_Thesis.pdf - Accepted Version Restricted to Repository staff only until 1 October 2025. Download (3MB) | Request a copy

Abstract

Eugenol 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 %.
===============================================================================================================================
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 %.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	eugenol, 1,3,4-Oxadiazola, karbon disulfida, carbon disulfide
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions:	Faculty of Science and Data Analytics (SCIENTICS) > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Hamida Azza Agistya
Date Deposited:	08 Aug 2023 03:05
Last Modified:	28 Aug 2023 02:36
URI:	http://repository.its.ac.id/id/eprint/103521

Actions (login required)

View Item