Vanillin → 1,5-Bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one
Reaction equation
O=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1>CC(C)=O>[OH:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[CH:4][C:5](=[O:6])[CH:8]=[CH:2][C:3]2[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=2)=[CH:4][C:5]=1[O:6][CH3:7]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
From vanillin and acetone in a 2:1 molar rate in acid medium, in temperatures that changes between 25 and 60° C., under ultrasonic irradiation conditions in a range from 25 to 40 KHz for a period of 1 to 3 hours further putting the reacted mixture into water/ice until producing the raw product, which dissolves in a solution of sodium hydroxide or potassium hydroxide (between 10-30%) being filtered; the filtrated is treated with hydrochloric acid or sulphuric acid from a concentration between 10-30%, the obtained product being filtered again, finally it is washed with distillated water until obtaining a neutral pH, this operation being repeated until the total purification of the product, not being necessary to perform a new purification of the compound using other procedures such as recrystallization or chromatographic column (the purity was determined by means of the HPLC technique):
Sources & evidence
- ORD record
- ord-b60e0fd664134ee99180b21a69ccab2d
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07432401B2
Reaction notes
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