Ethanol → 3-Methoxy-4-(methoxymethoxy)benzaldehyde
Reaction equation
O[C:2]1[C:7](CC=C(C)C)=[C:6]([O:13][CH2:14][O:15][CH3:16])[CH:5]=[C:4](OCOC)[C:3]=1[C:21](=[O:23])C.[CH2:24]([OH:26])C>>[CH3:24][O:26][C:7]1[CH:2]=[C:3]([CH:4]=[CH:5][C:6]=1[O:13][CH2:14][O:15][CH3:16])[CH:21]=[O:23]Participants
Procedure
In 95.0 ml of ethanol were dissolved 14.8 g of the 2'-hydroxy-4',6'-bis(methoxymethoxy)-3'-(3-methyl-2butenyl)acetophenone obtained in Production Example 1 and 9.0 g of the 3-methoxy-4-methoxymethoxybenzaldehyde obtained in Production Example 17, the solution was cooled to 0° C., and 138.0 ml of a saturated solution of potassium hydroxide in ethanol was added to the solution. The temperature was elevated to room temperature and the reaction liquid was stirred for 15 hours. The reaction liquid was made acidic by an addition of hydrochloric acid and extracted with diethyl ether. The ether layer was concentrated under a reduced pressure. The reaction mixture was subjected to the column chromatography [230-400 mesh Kieselgel 60; eluting solvent=hexane/ethyl acetate (3/1)] to obtain 13.1 g (yield=57.0%) of 2'-hydroxy-3-methoxy-4,4',6'-tris(methoxymethoxy)-3'-(3-methyl-2-butenyl)chalcone.
Sources & evidence
- ORD record
- ord-17173d2756f0416bb6d3d4104b6a35e5
- Source dataset
- uspto-grants-1993_08
- Patent number
- US05234951
Reaction notes
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