Synthesis 1,2-bis ((3-methylbut-2-en-1-yl)oxy) -4-(((3methylbut-2-en-1-yl)oxy)methyl)benzene

Abstract

Kojic acid and arbutin are materials that are used to inhibit melanogenesis, but in their development, these two compounds have an adverse effect on the skin. 3,4-dihydroxybenzaldehyde is a simple phenol compound whose derivatives are used as flavorers and fragrance. The research carried out aims to obtain 3,4-dihydroxybenzaldehyde derivatives in the form of 1,2-bis((3-methylbut-2-en-1-yl)oxy) 4-(((3-methylbut-2-en-1-yl)oxy)methyl)benzene which is estimated based on its structure is able to inhibit melanogenesis, and has a similar structure to the commercial fragrance of methyl diantilis. The synthesis of the target compound is carried out in three step. The first step involves the alkylation of 3,4-dihydroxybenzaldehyde with 3,3-dimethylalyl bromide and sodium hydride in the dimethylformamide solvent at room temperature to obtain 3,4-bis ((3-methylbut-2-en-1-il) benzaldehyde. Reduction of formyl 3,4-bis((3-methylbut-2-en-1-il) benzaldehyde which is carried out in the second stage with sodium borohydride in ethanol obtained 3,4-bis((3-methylbut-2-en-1-yl)oxy)phenyl)methanol. Etherification 3,4-bis ((3-methylbut-2-en-1-il)oxy)phenyl)methanol with 3,3-dimethylalyl bromide and sodium hydride in the solvent dimethylformamide at room temperature is obtained target compound 1,2-bis((3-methylbut-2-en-1-il)oxy)-4-(((3-methylbut-2-en-1 il)oxy)methyl)benzene whose structure is determined by NMR, mass, and IR spectroscopy.