Sintesis 2-(4-Alil-2-Metoksifenoksi)-N'-(4-Hidroksi-3-Metoksibenziliden)Asetohidrazida

Masitoh, Heni (2023) Sintesis 2-(4-Alil-2-Metoksifenoksi)-N'-(4-Hidroksi-3-Metoksibenziliden)Asetohidrazida. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Eugenol 1 merupakan senyawa fenolik dengan substituen alil, hidroksil, dan metoksi yang dapat ditransformasi menjadi beberapa turunan yang bermanfaat secara langsung atau menjadi bahan dasar untuk pembuatan senyawa lain. Eugenol 1 dan turunanya telah dilaporkan memiliki aktivitas biologis seperti antiseptik, antijamur, antibakteri, antiinflamasi, dan antioksidan. Transformasi eugenol 1 dapat dilakukan melalui alkilasi, adisi, asetilasi, esterifikasi, siklisasi monoeter, dan sebagainya. Modifikasi lain juga dapat dilakukan sehingga menghasilkan senyawa kelompok benzilidena yang mengandung gugus azometin (CO-NH-N=CH) yang juga aktif secara biologis. Penelitian yang dilakukan bertujuan untuk mendapatkan senyawa 2-(4-alil-2-metoksifenoksi N'-(4-hidroksi-3-metoksibenziliden)aseto-hidrazida 15 melalui modifikasi eugenol 1. Penelitian dilakukan melalui sintesis etil 2-(4-alil-2-metoksifenoksi)asetat 19, 2-(4-alil-2-metoksifenoksi)asetohidrazida 17 yang dilanjutkan reaksi dengan 4-hidroksi-3-metoksibenzaldehida 16. Penelitian yang dilakukan telah berhasil mendapatkan etil 2-(4-alil-2-metoksifenoksi)asetat 19 dengan rendemen 69 % melalui alkilasi eugenol 1 dengan etil kloro asetat 20. Selanjutnya, 2-(4-alil-2-metoksifenoksi)asetohidrazida 17 dengan rendemen 61% telah diperoleh melalui antara etil 2-(4-alil-2-metoksifenoksi)asetat 19 dengan hidrazin hidrat 18. N'-(4-Hidroksi-3-metoksibenziliden)asetohidrazida 15 dengan rendemen 39% selanjutnya telah berhasil diperoleh melalui reaksi etil 2-(4-alil-2-metoksifenoksi)asetat 19 dengan 4-hidroksi-3-metoksibenzaldehida 16.
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Eugenol 1 is a phenolic compound with allyl, hydroxyl and methoxy substituents which can be transformed into several useful derivatives directly or become basic materials for the manufacture of other compounds. Eugenol 1 and its derivatives have been reported to have biological activities such as antiseptic, antifungal, antibacterial, anti-inflammatory and antioxidant. Eugenol 1 transformation can be carried out through alkylation, addition, acetylation, esterification, monoether cyclization, and so on. Other modifications can also be made to produce a benzylidene group compound containing an azomethine group (CO-NH-N=CH) which is also biologically active. The aim of the research was to obtain 2-(4-allyl-2-methoxyphenoxy N'-(4-hydroxy-3-methoxybenzyliden)acetohydrazide 15 by modifying eugenol 1. The research was carried out by synthesizing ethyl 2-(4-allyl-2-methoxy- phenoxy)acetate 19, 2-(4-allyl-2-methoxyphenoxy)acetohydrazide 17 followed by reaction with 4-hydroxy-3-methoxybenzaldehyde 16. Research has succeeded in obtaining ethyl 2-(4-allyl-2-methoxyphenoxy )acetate 19 in 69% yield via alkylation of eugenol 1 with ethyl chloro acetate 20. Furthermore, 2-(4-allyl-2-methoxyphenoxy)acetohydrazide 17 in 61% yield was obtained via ethyl 2-(4-allyl-2- methoxyphenoxy)acetate 19 with hydrazine hydrate 18. N'-(4-Hydroxy-3-methoxybenzyliden)acetohydrazide 15 with a yield of 39% was further obtained by the reaction of ethyl 2-(4-allyl-2-methoxyphenoxy)acetate 19 with 4- hydroxy-3-methoxy-benzaldehyde 16.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	eugenol, 4-hydroxy-3-methoxybenzaldehyde, benzylidene, purification, structure elucidation, eugenol, 4-hidroksi-3-metoksibenzaldehida, benzilidena, pemurnian, elusidasi struktur
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:	Heni Masitoh
Date Deposited:	16 Feb 2023 11:11
Last Modified:	16 Feb 2023 11:11
URI:	http://repository.its.ac.id/id/eprint/97456

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