Formaldehyde → HCID 19082707, compound

A solution of potassium tertiary-butylate (90 mg, 0.8 mmol) in tert.-butanol (1 ml, synthesis quality, 99%) was added to a mixture of 2,4-dichloro-6-nitrotoluene (1.03 g, 5 mmol) and paraformaldehyde (150 mg, 5 mmol) in DMSO (2.5 ml, synthesis quality, additionally dried for 2 d over molecular sieve 4 Å). After the addition of the potassium tertiary-butylate solution, a color change from yellow to deep violet occurred. It was stirred for 5 min at room temperature and for 30 min at 70° to 80° C. (oil bath temperature). The mixture was then allowed to cool to room temperature and neutralized with a few drops of conc. HCl. The mixture was diluted with EtOAc (30 ml) and washed with H2O (30 ml). The aqueous phase was post-extracted with EtOAc (2×30 ml). Drying the organic phases over Na2SO4, filtering and evaporating the solvent under reduced pressure yielded the crude product which was purified by column chromatography (20 g SiO2, 12×2 cm, solvent: PE 30 ml, PE/EtOAc 10:1 110 ml, 9:1 100 ml, 8:1 360 ml, 7:1 80 ml). 2-(2,4-dichloro-6-nitrophenyl)ethanol (769 mg, 65%) was obtained as a yellow solid.

1. custom2.5 ml, synthesis quality
2. customadditionally dried for 2 d over molecular sieve 4 Å)
3. additionAfter the addition of the potassium tertiary-butylate solution
4. temperatureto cool to room temperature and neutralized with a few drops of conc. HCl
5. additionThe mixture was diluted with EtOAc (30 ml)
6. washwashed with H2O (30 ml)
7. extractionThe aqueous phase was post-extracted with EtOAc (2×30 ml)
8. dry with materialDrying the organic phases over Na2SO4
9. filtrationfiltering
10. customevaporating the solvent under reduced pressure
11. customyielded the crude product which
12. customwas purified by column chromatography (20 g SiO2, 12×2 cm, solvent: PE 30 ml, PE/EtOAc 10:1 110 ml, 9:1 100 ml, 8:1 360 ml, 7:1 80 ml)

ORD record

ord-5956b7144d234fa69e2358b882627443

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05763599