4-Nonylphenol → Benzaldehyde, 2-hydroxy-5-nonyl-

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Reaction Steps

Ethylmagnesium bromide (18 ml of 3M solution in diethyl ether) was added dropwise to a stirred solution of 4-nonylphenol (11.2 g) in diethyl ether (100 ml) at 0°-10° C. under nitrogen. Stirring was continued at 10° C. for 30 minutes, the mixture was allowed to warm to ambient temperature, the bulk of the diethyl ether was removed by distillation, toluene (100 ml) and methanol (6.5 g) were added and removal of diethyl ether and free (uncoordinated to Mg) methanol was continued by fractional distillation with vigorous stirring until the temperature of the mixture rose to 100°-105° C. The mixture was cooled to 95° C. and a slurry of paraformaldehyde (6 g) in toluene (12 ml) was added dropwise over 20 minutes, the temperature of the reaction mixture being maintained at 95°-100° C. with removal of volatile by-products by distillation. Stirring was continued at 95°-100° C. for 2 hours, the mixture was added to a cold stirred solution of sulphuric acid (12 g of 98% strength material) in water (500 ml) at 10° C., the resulting mixture was stirred at 20°-30° C. for 2 hours, the mixture was filtered and the upper organic layer separated from the lower aqueous layer. The organic layer was washed with water (3×50 ml) and solvent was removed by evaporation under reduced pressure to give crude 2-hydroxy-5-nonylbenzaldehyde.

Provenance & Evidence