2'-Hydroxy-4',6'-bis(methoxymethoxy)-3'-(3-methyl2-butenyl)acetophenone → 4-(Methoxymethoxy)benzaldehyde

HRID 1030736

Reaction equation

HRID 1030736 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>CO>[CH3:16][O:15][CH2:14][O:13][C:6]1[CH:7]=[CH:2][C:3]([CH:21]=[O:23])=[CH:4][CH:5]=1

Participants

3

Procedure

In 30 ml of methanol were dissolved 14.73 g of the 2'-hydroxy-4',6'-bis(methoxymethoxy)-3'-(3-methyl-2-butenyl)acetophenone obtained in Production Example 13 and 7.55 g of the p-methoxymethoxybenzaldehyde obtained in Production Example 25, and a saturated solution of sodium hydroxide in methanol was added to the solution and the mixture was stirred at room temperature for 1 day to effect a reaction. After the reaction, the reaction mixture was carefully neutralized with dilute hydrochloric acid and extracted with 1.5 l of ethyl acetate, and the ethyl acetate layer was washed with water (500 ml×4 times), shaken with a saturated aqueous solution of sodium chloride (300 ml×2 times), dried with anhydrous sodium sulfate and filtered. The solvent was removed from the filtrate by distillation to obtain 18.94 g (yield=88.2%) of 2'-hydroxy-4,4',6'-tris(methoxymethoxy)-3'-(3-methyl-2-butenyl)chalcone in the form of a yellow oil.

Sources & evidence

ORD record
ord-9cc7bd3ea8fa447caaca978128feddea
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Linked notes

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