Kholidah Febriani (2020) Pengaruh Halangan Sterik Pada Reaksi Sintesis Asam O-Asetoksisinamat Dan Asam O-Butiriloksisinamat Menggunakan Iradiasi Gelombang Mikro. Skripsi thesis, UNIVERSITAS AIRLANGGA.

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Abstract

In recent years, derivatization of 2-hydroxycinamic acid or o-coumaricacid has become an important area of drug development. On the other hand,the steric hindrace is one of the most determining factor in organic synthesis.This research developed two ester derivatives of o-coumaric acid, i.e. oacetoxycinnamicacid and o-butyryloxycinnamic acid, through raction withactyl and butiryl chloride. The purpose of this study was to determine theeffect of steric hindrance on the microwave assisted acyl nucleophilicsubstitution to form esters from o-coumaric acid using acyl halidas. Thereaction was carried out at a power of 120-Watts and using 14 mmol of acylhalidas. o-acetoxycinnamic acid was completely formed at 1x30 secondswith a yield of 97,52 %, ± 0,79 greater than the percent yield of obutyryloxycinnamicacid, where the synthesis of o-butyryloxycinnamic acidtook 2x30 seconds to achieve complete reaction with a yield of 94,36 % ±0,44. Statistical analysis shows a significance value of 0.008 which is lessthan 0.05. This means that there are significant differences in the use of acylchloride in the form of acetyl chloride and butyryl chloride with the use ofacetyl chloride as reagent will result in a higher percent yield. That is, sterichindrance will have an influence in the esterification reaction between ocoumaricacid and acyl halidas. The greater the steric hindrance the longerthe reaction will take and yield of the results obtained will be less.The characteristics of the target compounds were carried out using FTIRspectrophotometry and 1H-NMR spectrometry. These characterizationshave shown that o-acetyloxycinnamic acid and o-butyryloxycinnamic acidhave been successfully synthesized.

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