Sintesis 2-(4-alil-2-metoksifenoksi)-N'-(4-metoksibenzilidena)asetohidrazida

Arista, Dias Nur (2023) Sintesis 2-(4-alil-2-metoksifenoksi)-N'-(4-metoksibenzilidena)asetohidrazida. Other thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Eugenol 1 yang memiliki gugus fungsional alil (-CH2-CH=CH2), hidroksil (-OH), dan metoksi (-OCH3) merupakan senyawa fenolik alami yang terdapat pada minyak atsiri dan ekstrak beberapa tumbuhan. Eugenol 1 dan turunannya menunjukkan aktivitas biologis menarik seperti antioksidan, antiinflamasi, antispasmodik, antidepresan, antigenotoksik, antikarsinogenik, dan antijamur. Turunan eugenol teralkilasi menunjukkan aktivitas biologis yang lebih baik daripada eugenol 1. Modifikasi eugenol 1 dengan penambahan gugus benzilidena dilaporkan juga dapat meningkatkan aktivitas eugenol 1. Penelitian yang dilakukan bertujuan untuk mendapatkan 2-(4-alil-2-metoksifenoksi)-N'-(4-metoksibenzilidena)asetohidrazida 16 dengan modifikasi eugenol 1 melalui alkilasi, penambahan gugus amina, dan penambahan aldehida. Penelitian dilakukan melalui sintesis etil 2-(4-alil-2-metoksifenoksi)asetat 20 dan 2-(4-alil-2-metoksifenoksi)asetohidrazida 17 yang dilanjutkan reaksi dengan 4-metoksibenzaldehida 18. Penelitian yang dilakukan telah berhasil mendapatkan etil 2-(4-alil-2-metoksifenoksi)asetat 20 dengan rendemen 69% melalui reaksi antara eugenol 1 dengan etil kloro asetat 21. Senyawa 2-(4-alil-2-metoksifenoksi)asetohidrazida 17 juga telah berhasil diperoleh dengan rendemen 61% melalui reaksi etil 2-(4-alil-2-metoksifenoksi)asetat 20 dengan hidrazin hidrat 19. 2-(4-Alil-2-metoksifenoksi)-N'-(4-metoksibenzilidin)asetohidrazida 16 dengan rendemen 38% diperoleh dari 2-(4-alil-2-metoksifenoksi)asetohidrazida 17 dan 4-metoksibenzaldehida 18. ======================================================================================================================================
Eugenol 1 is a phenolic compound that occurs naturally in several plant extracts. Eugenol 1 contains allyl functional groups (-CH2-CH=CH2), hydroxy (-OH) and methoxy (-OCH3). The natural product eugenol 1 has demonstrated several interesting biological activities such as antioxidant, anti-inflammatory, antispasmodic, antidepressant, antigenotoxic, anticarcinogenic and antifungal. Various alkylated eugenol derivatives have shown better performance than eugenol 1 in its natural form, some of which are α-D-glucosylated eugenol and Ibuprofen-eugenol. Modification of eugenol 1 with benzylidene substituents will increase the activity of eugenol 1. The presence of benzylidene compounds will increase biological activities such as anticonvulsant, antidepressant, analgesic, anti-inflammatory, antimalarial, antimicrobial, antimicrobial, antiviral, and antitumor. The purpose of the research was to obtain 2-(4-allyl-2-methoxyphenoxy)-N'-(4-methoxybenzylidene)acetohydrazide 16 with modification of the hydroxy group of eugenol 1 through alkylation, followed by amidation and addition of aldehydes. The research was conducted through the syntesis of ethyl 2-(4-alyl-2-methoxyphenoxy)acetate 20 with a yield of 69% through the Williamson reaction mechanism by eugenol 1 and ethyl chloro acetate 21 followed by the addition of potassium carbonate. 2-(4-allyl-2-methoxyphenoxy)acetohydrazide 17 was also been obtained in 61% yield through the nucleophilic addition reaction following the Wolff-Kishner reaction mechanism by ethyl 2-(4-allyl-2-methoxyphenoxy)acetate 20 and hydrazine hydrate 19. Finally, the final product 2-(4-allyl-2-methoxyphenoxy)-N'-(4-methoxybenzylidin)acetohydrazide 16 with a yield of 38% have been successfully obtained through the nucleophilic addition reaction mechanism follows the Wolff-Kishner reaction by 2-(4-allyl -2-methoxyphenoxy)acetohydrazide 17 and 4-methoxybenzaldehyde 18 with the addition of acetic acid.

Item Type:	Thesis (Other)
Uncontrolled Keywords:	eugenol, 4-metoksibenzaldehida, benzilidena, eugenol,.benzylidene, alkylation, amidation
Subjects:	Q Science > QD Chemistry > QD251.2 Chemistry, Organic. Biochemistry
Divisions:	Faculty of Natural Science > Chemistry > 47201-(S1) Undergraduate Thesis
Depositing User:	Dias Nur Arista
Date Deposited:	17 Feb 2023 11:32
Last Modified:	17 Feb 2023 11:32
URI:	http://repository.its.ac.id/id/eprint/97514

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