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

HRID 2254239Notes

Reaction equation

HRID 2254239 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-6b4188332a5f4308ab523bb1cbc3adee
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

Loading…