Synthesis of 4-(5-bromo-4-hydroxyphenyl-3-methoxy)-2-butanone and the activity test as fruit flies attractant

Synthesis of 4-(5-bromo-4-hydroxyphenyl-3-methoxy)-2-butanone and its potential test as fruit flies attractant has been done. Synthesis of 4-(5-bromo-4-hydroxyphenyl-3-methoxy)-2- butanone was carried out in three steps reactions. First, the bromination of vanillin was performed using KBrO3 and HBr in acidic conditions. Second, aldol condensation of 5-bromovanillin with acetone using base catalyst NaOH 20. Third, 4-(5-bromo-4-hydroxyphenyl-3-methoxy)-2- butanone was synthesized by reduction of condensation aldol products with NaBH4 and NiCl2.6H2O in methanol under mild condition. All of the products were analyzed by FT-IR, GC-MS, and 1HNMR spectrometers. Based on these analyses, the synthesis of 4-(5-bromo-4-hydroxyphenyl-3- methoxy)-2-butanone has been done successfully by selective hydrogenation reaction in 68 yield. The activity test showed that the synthesized compound could be used as an attractant of fruit fly. © 2020 Trans Tech Publications Ltd, Switzerland.