Dimethyl Sulfate → 1-(Methoxymethyl)-2-nitrobenzene

HRID 339004

Reaktionsgleichung

Reaktionsgleichung von HRID 339004
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][OH:11])([O-:3])=[O:2].[OH-].[Na+].[CH3:14]OS(OC)(=O)=O>C(Cl)Cl.O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:14][O:11][CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Komponenten

7

Edukt 3

HCID 6497Dimethyl SulfateHCID 119232-Nitrobenzyl alcoholHCID 14798Sodium Hydroxide

Produkt 1

HCID 126166891-(Methoxymethyl)-2-nitrobenzeneAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of (2-nitrophenyl)methanol (5.13 g, 33.50 mmol) in DCM (75 mL) was added 3.35 N NaOH (75 mL, 251.2 mmol) in water at ambient temperature and stirred at ambient temperature for 10 minutes. Me2SO4 (6.38 ml, 67.0 mmol) and tetrabutylammonium hydrogen sulfate (0.57 g, 1.68 mmol) were added and the mixture stirred vigorously for 20 hours at ambient temperature. The reaction mixture was diluted with DCM (100 mL) and organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate) to give 1-(methoxymethyl)-2-nitrobenzene (5.12 g, 91.4%) as an oil.

Aufarbeitung

  1. stirringthe mixture stirred vigorously for 20 hours at ambient temperature
  2. customwas separated
  3. washwashed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-3ce3c4966cc3415d84870434888c0353
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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