4-Nitrophenol → 4-(2-Hydroxy-1-decyloxy)nitrobenzene

Temperatur

100 °C

The sodium salt of 4-nitrophenol (28.19 g, 0.175 mol) was dissolved in water (50 mL) and toluene (300 mL) and tetrabutylammonium sulfate (6.0 g) was added. 1,2-Epoxydecane (27.3 g, 0.175 mol) was added to this mixture and the reaction was heated at 100° C. for 5 days. The toluene layer was separated and washed with water (4×75 mL), 1N hydrochloric acid (2×75 mL) and water (75 mL). The organic layer was dried over sodium sulfate, filtered and the solvent removed. The crude product was purified by silica gel chromatography (2-3% methanol/methylene chloride) to afford 4-(2-hydroxy-1-decyloxy)nitrobenzene as a pale oil (20 g, 0.68 mol, 39% yield).

1. customThe toluene layer was separated
2. washwashed with water (4×75 mL), 1N hydrochloric acid (2×75 mL) and water (75 mL)
3. dry with materialThe organic layer was dried over sodium sulfate
4. filtrationfiltered
5. customthe solvent removed
6. customThe crude product was purified by silica gel chromatography (2-3% methanol/methylene chloride)

ORD-Eintrag

ord-81dbb5e70efa4827874fde291b252acd

Quelldatensatz

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07704667B2