Tuesday, April 22, 2008

How to Synthesize o-ethoxybenzaldehyde from phenol, methanol, and hydrochloric acid

Take the methanol and add 10% hydrochloric. This will form methylchloride. Then, react the methyl chloride with phenol in aluminum chloride (AlCl3). This will form o-methylphenol. React with sodium hydride, which will remove the proton from the hydroxy group, and react with methylchloride to perform an SN2 reaction. React the compound with KMnO4, forming o-ethoxybenzoic acid. Then, react with LiAlH4 in water, turning the carboxylic acid to an alcohol. React again with PCC, and you have your compound- o-ethoxybenzaldehyde, a structural analogue to vanillin.

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