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Author: Subject: Preparation of Crude 2-Hydroxy-5-Methoxybenzaldehyde. Methanol?
Cookie Monster

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biggrin.gif posted on 11-6-2021 at 12:50
Preparation of Crude 2-Hydroxy-5-Methoxybenzaldehyde. Methanol?

Hi, this about patent
“ Example 1 Preparation of Crude 2-Hydroxy-5-Methoxybenzaldehyde.
A mixture of 600 g of acetonitrile, 186.2 g of 4-methoxyphenol (1.5 moles) and 214 g (2.25 moles) of anhydrous magnesium chloride was warmed to 45° C. and 227.4 g (2.25 moles) of triethylamine was added dropwise at that temperature. Paraformaldehyde (150 g, 4.75 moles) was then added and the reaction was heated to reflux. Methanol was removed over 3 hours by distillation, using a 10-inch column packed with Penn-State packing. “

Where does methanol come from? Of the reaction? Forgot to add it at the beginning?

De donde sale el metanol? De la reacción? Se han olvidado añadirlo al principio?.

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[*] posted on 11-6-2021 at 12:56

Reduction of the formaldehyde, I suppose.
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[*] posted on 11-6-2021 at 13:57

This looks like a similar reaction to the Casiraghi formylation, whose mechanism and scope are detailed here:

If that link doesn't work directly, the paper is Selective reactions between phenols and formaldehyde. A novel route to salicylaldehydes. Journal of the Chemical Society, Perkin Transactions 1, 1862. doi:10.1039/p19800001862
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