Nitric Acid → HCID 13895882, compound

HRID 963765Notes

Reaction equation

[N+:1]([O-:4])(O)=[O:2].[CH2:5]([OH:17])[CH2:6][C:7]1[CH:16]=[CH:15][C:12]([O:13][CH3:14])=[C:9]([O:10][CH3:11])[CH:8]=1.C([O-])(O)=O.[Na+]>C(O)(=O)C.O>[CH3:14][O:13][C:12]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([CH2:6][CH2:5][OH:17])=[C:16]([N+:1]([O-:4])=[O:2])[CH:15]=1

Participants

Conditions

Temperature: -10 °C

Procedure

For 6 min, conc. HNO3 (4.8 ml, 65%, d=1.4) was added dropwise to a mixture of homoveratryl alcohol (3.02 g, 16.6 mmol) in glacial acetic acid (30 ml) under stirring, this mixture having been cooled to -10° C. (common salt/ice) It was then allowed to warm up to 23° C. in 30 min. After being stirred for 1 h at this temperature, the mixture was diluted with H2O, neutralized with NaHCO3 and extracted with EtOAc (3×30 ml). The combined organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue (3.25 g) was purified by column chromatography (90 g SiO2 toluene/EtOAc 4:1 500 ml, toluene/EtOAc 3:1 400 ml, toluene/EtOAc 2:1 300 ml). 2-(4,5-dimethoxy-2-nitrophenyl)ethanol (2.13 g, 56%) was obtained as a yellow solid.

Workup

temperatureto warm up to 23° C. in 30 min
stirringAfter being stirred for 1 h at this temperature
extractionextracted with EtOAc (3×30 ml)
dry with materialThe combined organic phases were dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue (3.25 g) was purified by column chromatography (90 g SiO2 toluene/EtOAc 4:1 500 ml, toluene/EtOAc 3:1 400 ml, toluene/EtOAc 2:1 300 ml)

Sources & evidence

ORD record: ord-646ba4b40d2c42e48ba7138bda8369d6
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05763599

Reaction notes

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