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

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.

1. customthe bulk of the diethyl ether was removed by distillation, toluene (100 ml) and methanol (6.5 g)
2. additionwere added
3. customremoval of diethyl ether and free (uncoordinated to Mg) methanol
4. distillationwas continued by fractional distillation
5. stirringwith vigorous stirring until the temperature of the mixture
6. customrose to 100°-105° C
7. temperatureThe mixture was cooled to 95° C.
8. additiona slurry of paraformaldehyde (6 g) in toluene (12 ml) was added dropwise over 20 minutes
9. temperaturethe temperature of the reaction mixture being maintained at 95°-100° C. with removal of volatile by-products by distillation
10. stirringStirring
11. waitwas continued at 95°-100° C. for 2 hours
12. additionthe mixture was added to a cold stirred solution of sulphuric acid (12 g of 98% strength material) in water (500 ml) at 10° C.
13. stirringthe resulting mixture was stirred at 20°-30° C. for 2 hours
14. filtrationthe mixture was filtered
15. customthe upper organic layer separated from the lower aqueous layer
16. washThe organic layer was washed with water (3×50 ml) and solvent
17. customwas removed by evaporation under reduced pressure

ORD record

ord-950b41fc0ae4450dbfbb918817886352

Source dataset

uspto-grants-1994_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05354920