Formaldehyde → Benzaldehyde, 2-hydroxy-5-nonyl-

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A solution of magnesium methoxide (292 g of 8% solution in methanol, 0.275 mol) was added over 10 minutes to a stirred solution of p-nonylphenol (55 g, 0.25 mol) in methanol (50 ml). The stirred mixture was heated to reflux temperature, the bulk of the methanol was removed by distillation, toluene (500 ml) was added and toluene:methanol azeotrope was removed by fractional distillation until the temperature of the reaction mixture rose to 100° C. The mixture was cooled to 90° C. and an agitated slurry of paraformaldehyde fine powder (26.25 g, 0.875 mol) in toluene (100 ml) was added evenly over 1 hour to the reaction mixture at 90°-100° C. with removal of volatile by-products by distillation. Stirring was continued at 100° C. for a further hour, the mixture was cooled to 45° C. and was added to a premixed solution of concentrated sulphuric acid (62.5 g, 0.875 mol) in water (1 liter). The resulting mixture was stirred at ambient temperature for 1 hour, the phases were separated and the aqueous phase was extracted with toluene (200 ml). The toluene extract was combined with the original organic phase and toluene was removed by distillation under reduced pressure to give the crude 2-hydroxy-5-nonyl benzaldehyde as a yellow oil (58.5 g).

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