HCID 11172502, compound → 4-(Methoxymethoxy)benzaldehyde

HRID 1030744Notes

Reaction equation

HRID 1030744 reaction equation
COCO[C:5]1[CH:10]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[C:15](=[O:17])C>C(O)C>[CH3:14][O:13][CH2:12][O:11][C:9]1[CH:10]=[CH:5][C:6]([CH:15]=[O:17])=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 11172502HCID 11172502, compound

Product 1

HCID 2500744-(Methoxymethoxy)benzaldehydeYield 91.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 50 ml of ethanol were dissolved 6.31 g of the 2',4'-bis(methoxymethoxy)acetophenone obtained in Production Example 10 and 4.00 g of the p-methoxymethoxybenzaldehyde obtained in Production Example 25, and the solution was cooled to 0° C. and 30 ml of a saturated solution of potassium hydroxide in ethanol was added to the solution. The temperature of the reaction liquid was elevated to room temperature and the liquid was stirred for 2 days. The reaction liquid was diluted with water, neutralized with 6N hydrochloric acid and extracted with ethyl acetate, and the organic layer was dried with sodium sulfate and concentrated under reduced pressure to obtain a reaction mixture in the form of a syrup. The syrup was subjected to the column chromatography (320 g of 270-400 mesh Kieselgel 60; 0.5 kg/cm2 ; eluting solvent: hexane/ethyl acetate=1). Fractions of 50 ml were collected and the 66th to 87th fractions were combined to obtain 5.64 g (yield=55.9 %) of 2',4,4'-tris(methoxymethoxy)chalcone.

Sources & evidence

ORD record
ord-772e6235962e48f990747f07b40580ca
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

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