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

HRID 1030723Notes

Reaction equation

HRID 1030723 reaction equation
O[C:2]1[C:7](CC=C)=[C:6]([O:11][CH2:12][O:13][CH3:14])[CH:5]=[C:4](OCOC)[C:3]=1[C:19](=[O:21])C>C(O)C>[CH3:14][O:13][CH2:12][O:11][C:6]1[CH:7]=[CH:2][C:3]([CH:19]=[O:21])=[CH:4][CH:5]=1

Participants

3

Reactant 1

HCID 197448852'-Hydroxy-4',6'-bis(methoxymethoxy)-3'-(2-propenyl)acetophenone

Product 1

HCID 2500744-(Methoxymethoxy)benzaldehydeYield 119.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 40 ml of ethanol were dissolved 20.4 g of the 2'-hydroxy-4',6'-bis(methoxymethoxy)-3'-(2-propenyl)acetophenone obtained in Production Example 6 and 13.7 g of the p-methoxymethoxybenzaldehyde obtained in Production Example 23, and a 50% solution of potassium hydroxide in ethanol was added to the solution and the mixture was stirred at room temperature overnight to effect a reaction. After the reaction, the reaction mixture was neutralized with dilute hydrochloric acid and extracted with ethyl acetate, and the solvent was removed from the ethyl acetate layer by distillation. The obtained residue was crystallized from methanol to obtain 26.3 g (yield=85.9%) of 2'-hydroxy-4,4',6'-tris(methoxymethoxy)-3'-(2-propenyl)chalcone in the form of a yellow prism.

Sources & evidence

ORD record
ord-e48f351ce1db4610bf295951ff9c8b26
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

Loading…