HCID 11172502, compound → 4-(Methoxymethoxy)benzaldehyde

HRID 2254261Notes

Reaction equation

HRID 2254261 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 6 N 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=1/1). 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-b0c34ea67d5643a5a8cf19c5701cdbf7
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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