This study was an experimental study aimed to obtain the optimal time in the synthesis of chalcone compounds through cross aldol condensation reaction. The starting materials used were vanillin, p-nitroacetophenone, and acid catalyst. The study began by reacting vanillin and p-nitroacetophenone in HCl catalyst and the flow of nitrogen. The optimalization of reaction time was done in some variation of time, 3 hours, 5 hours and 7 hours. The reaction products were recrystallized with solvents mixture aquades: ethanol (1:1). Recrystallization product then checked by TLC using mixed eluents n-hexane: ethyl acetate (4:1). The products of the study were powder with the appropriate weight range and yield of the reaction time (3 hours, 5 hours and 7 hours) was 0.16 g: 5.387%, 0.48 grams: 16.162% and 0.43 grams: 14.478%. the optimum time for this reaction was 5 hours. Key words: condensation, vanillin, p-nitroacetophenone, acid catalyst
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