Formaldehyde → 5-Methoxy-2-nitrobenzeneethanol

Triton B (2 ml, 35% in MeOH) was added at 80° C. to a mixture of 5-methoxy-2-nitrotoluene (25 g, 150 mmol) and paraformaldehyde (2.3 g, 73 mmol) in DMSO (20 ml, synthesis quality, additionally dried for 2 d over molecular sieve 4 Å). After being stirred 2.5 h at this temperature, it was cooled to room temperature and neutralized with a few drops of conc. HCl. The mixture was diluted with H2O (50 ml) and extracted with EtOAc (5×100 ml). The organic phases were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was subjected to a distillation in a high vacuum (p=0.1 torr), whereby a fraction containing starting material (12.1 g) was obtained at 70° C. The residual crude product was purified by column chromatography (240 g SiO2, solvent: toluene/EtOAc 8:1 1400 ml, 7:1 1600 ml, 6:1 400 ml, 5:1 400 ml, 3:1 400 ml, 2:1 600 ml and 1:1 600 ml). 2-(5-methoxy-2-nitrophenyl)ethanol (6.87 g, 48%) was obtained as a yellow oil.

1. custom20 ml, synthesis quality
2. customadditionally dried for 2 d over molecular sieve 4 Å)
3. additionThe mixture was diluted with H2O (50 ml)
4. extractionextracted with EtOAc (5×100 ml)
5. dry with materialThe organic phases were dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. distillationThe residue was subjected to a distillation in a high vacuum (p=0.1 torr), whereby a fraction
9. additioncontaining
10. customwas obtained at 70° C
11. customThe residual crude product was purified by column chromatography (240 g SiO2, solvent: toluene/EtOAc 8:1 1400 ml, 7:1 1600 ml, 6:1 400 ml, 5:1 400 ml, 3:1 400 ml, 2:1 600 ml and 1:1 600 ml)

ORD record

ord-9321d65358aa4c67bb2772ddf2a46725

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05763599