2'-Hydroxy-4',6'-bis(methoxymethoxy)-3'-(3-methyl2-butenyl)acetophenone → 4-(Methoxymethoxy)-3-(3-methylbut-2-en-1-yl)benzaldehyde
Reaction equation
O[C:2]1[C:7]([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])=[C:6]([O:13][CH2:14][O:15][CH3:16])[CH:5]=[C:4](OCOC)[C:3]=1[C:21](=[O:23])C>C(O)C>[CH3:16][O:15][CH2:14][O:13][C:6]1[CH:5]=[CH:4][C:3]([CH:21]=[O:23])=[CH:2][C:7]=1[CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
In 45 ml of ethanol were dissolved 6.99 g of the 2'-hydroxy-4',6'-bis(methoxymethoxy)-3'-(3-methyl- 2-butenyl)acetophenone obtained in Production Example 13 and 5.01 of the 4-methoxymethoxy-3-(3-methyl-2-butenyl)benzaldehyde, and the solution was cooled to 0° C. Then, 65 ml of a saturated solution of potassium hydroxide in ethanol was added to the solution and the mixture was stirred at room temperature overnight. The reaction liquid was neutralized with 6 N hydrochloric acid and extracted with ethyl acetate, and the ethyl acetate layer was washed with water, dried with anhydrous sodium sulfate and filtered. The solvent was removed from the filtrate by distillation and the residue was recrystallized from n-hexane to obtain 7.22 g (yield=61.7%) of 2'-hydroxy-4,4',6'-tris(methoxymethoxy)-3,3'-bis(3-methyl-2butenyl)chalcone.
Sources & evidence
- ORD record
- ord-e951c54df41e4d16a535c70181c50693
- Source dataset
- uspto-grants-1993_08
- Patent number
- US05234951
Reaction notes
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