| Summary: | Synthesis of 3,4-dimethoxybenzyl acetate and methyl-(3,4-dimetoxy
phenyl) acetate from vanillin have been carried out. Both esters have an activity as attractant fruit flies Dacus dorsalis and Dacus curcubitae.
Synthesis of 3,4-dimethoxybenzyl alcohol was carried out via methylation
of vanillin followed by reduction. Vanillin methylation with dimethyl carbonate
(DMC) was performed under sonication. This reaction yielded 98,36% veratraldehyde. Veratraldehyde was then reduced at room temperature using
NaBH4 with stirring and sonication methods, yielded 97,00 and 98,87% 3,4-
dimethoxybenzyl alcohol, respectively.
3,4-Dimethoxybenzyl acetate was yielded 98.28% from esterification of
3,4-dimethoxybenzyl alcohol and acetic acid by the use of sulfuric acid as a
catalyst with sonication. Methyl-(3,4-dimethoxyphenyl) acetate was produced via 4 concecutive reactions, i.e. 1) chlorination of 3,4-dimethoxybenzyl alcohol with SOCl2 yielded 77,75% 3,4-dimethoxybenzyl chloride, 2) nitrilization of 3,4- dimethoxybenzyl chloride with NaCN in acetone yielded 66,16% 3,4-
dimethoxyphenyl acetonitrile, 3) the product was then hydrolyzed with HCl,
yielded 89,28% 3,4-dimethoxybenzyl carboxylate and 4) esterification of 3,4-
dimethoxybenzyl carboxylate using methanol and sulfuric acid as a catalyst by
sonication, yielded 95.23% yellowish viscous liquid of methyl-(3,4-
dimethoxyphenyl) acetate.
|
|---|