Water → HCID 4767210, compound

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Reaction Steps

5 g of sodium are dissolved in 200 ml of methanol. 30.4 g of vanillin are metered into the resulting solution. The reaction mixture is stirred at room temperature for 30 minutes. 36 g of 1-chloromethylnaphthalene in 70 ml of methanol are then added and the reaction mixture is heated at reflux for 6 hours. The mixture is left to stand overnight and then introduced into 1 liter of water. Extraction is carried out twice using 700 ml of ethyl acetate each time. The organic phases are washed twice using 200 ml of ice-cold 2N sodium hydroxide solution each time and once with 200 ml of saturated sodium chloride solution, dried over magnesium sulfate and concentrated, yielding 3-methoxy(naphthalen-1-ylmethoxy)-benzaldehyde, which can be purified by chromatography on silica gel with ethyl acetate/n-hexane 1:2 and recrystallisation from ethyl acetate/n-hexane, m.p. 98-99° C.

Provenance & Evidence