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

Temperature

95 °C

A 2 -liter round-bottomed flask was charged with magnesium (12 g, 0.49 mol), methanol (285 ml), toluene (120 mol) and magnesium methoxide (10 ml solution of 7.4% by weight magnesium methoxide in methanol). The reaction mixture was heated to reflux and the magnesium dissolved. Para-nonyl phenol (112.4 g) was added in one portion to the reaction mixture. The flask was then rigged for a fractional vacuum distillation and an azeotrope of methanol/toluene was distilled off to an internal temperature of 70° C. at a pressure of 350 mm Hg. Glacial acetic acid (28.5 ml, 0.5 mole) was added to the reaction mixture over a 1 hour period while maintaining the reaction temperatures at 70° C. and the pressure at 350 mm Hg. When the addition of glacial acetic acid was complete, pyridine (79 ml)and toluene (250 ml) were added. An azeotrope of methanol and toluene was distilled at pot temperature of 100° C. The reaction mixture was then cooled to 95° C. and solid paraformaldehyde (46 g, a commercial sample containing 5-7% by weight water) was added over a 45 minute period. The reaction mixture was maintained at a temperature of 95-100° C. during the addition of paraformaldehyde and volatile reaction by-products were continually removed by distillation. When the paraformaldehyde addition was complete, the reaction temperature was maintained at 95-100° C. for an additional 2 hours. Sulphuric acid (300 ml, 10% w/w) was added to the reaction mixture, which was then stirred for 1 hour. After phase separation, the organic phase was washed twice and 200 ml portions of water. The washed organic phase was then separated, dried and rendered free of the solvent to yield crude 5-nonyl salicylaldehyde. A 78% yield was obtained.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux
3. distillationThe flask was then rigged for a fractional vacuum distillation
4. distillationan azeotrope of methanol/toluene was distilled off to an internal temperature of 70° C. at a pressure of 350 mm Hg
5. temperaturewhile maintaining
6. customthe reaction temperatures at 70° C.
7. distillationAn azeotrope of methanol and toluene was distilled at pot temperature of 100° C
8. additionsolid paraformaldehyde (46 g, a commercial sample containing 5-7% by weight water)
9. additionwas added over a 45 minute period
10. temperatureThe reaction mixture was maintained at a temperature of 95-100° C. during the addition of paraformaldehyde and volatile reaction by-products
11. customwere continually removed by distillation
12. additionWhen the paraformaldehyde addition
13. temperaturethe reaction temperature was maintained at 95-100° C. for an additional 2 hours
14. additionSulphuric acid (300 ml, 10% w/w) was added to the reaction mixture, which
15. customAfter phase separation
16. washthe organic phase was washed twice
17. customThe washed organic phase was then separated
18. customdried

ORD record

ord-e3030035223f4984be940fc1d85d74ca

Source dataset

uspto-grants-2001_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06274068B1