Formaldehyde → HCID 19082710, compound

Paraformaldehyde (750 mg, 25 mmol) and DBU (1.85 ml, 12.4 mmol) were added to a solution of 2-nitrobenzylmethylether (4.18 g, 25 mmol) in DMSO (3.5 ml, synthesis quality, additionally dried for 2 d over molecular sieve 4 Å) and allowed to react at room temperature for 4 h. The pH value was adjusted from pH 9 to about pH 3.5 by means of a few drops of conc. AcOH. The mixture was diluted with CH2Cl2 (120 ml) and washed with H2O (80 ml). The aqueous phase was post-extracted with CH2 Cl2 (2×80 ml). The combined organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product (5.56 g) was purified by column chromatography (140 g SiO2, 21×4.2 cm, solvent: toluene 300 ml, toluene/EtOAc 20:1 210 ml, 15:1 160 ml, 10:1 220 ml, 15:2 170 ml, 6:1 210 ml, 5:1 180 ml, 4:1 400 ml, 3:1 240 ml, 2:1 240 ml). First 2-nitrobenzylmethylether (2.442 g, 58%) was eluted then 2-methoxy-2-(2-nitrophenyl)ethanol (1.696 g, 34% and 82% respectively, in relation to the consumed starting material).

1. custom3.5 ml, synthesis quality
2. customadditionally dried for 2 d over molecular sieve 4 Å) and
3. customto react at room temperature for 4 h
4. washwashed with H2O (80 ml)
5. extractionThe aqueous phase was post-extracted with CH2 Cl2 (2×80 ml)
6. dry with materialThe combined organic phases were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe crude product (5.56 g) was purified by column chromatography (140 g SiO2, 21×4.2 cm, solvent: toluene 300 ml, toluene/EtOAc 20:1 210 ml, 15:1 160 ml, 10:1 220 ml, 15:2 170 ml, 6:1 210 ml, 5:1 180 ml, 4:1 400 ml, 3:1 240 ml, 2:1 240 ml)
10. washFirst 2-nitrobenzylmethylether (2.442 g, 58%) was eluted

ORD record

ord-ceeeaa01865c4ed2a2e4c2a0b1cde0bf

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05763599