2-Chloro-5-nitrobenzyl alcohol → 3-Hydroxymethyl-4-(methylthio)nitrobenzene

HRID 396811

Reaktionsgleichung

Reaktionsgleichung von HRID 396811
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][OH:12].C(S)[CH2:14][S:15]([O-])(=O)=O.[Na+]>CS(C)=O.CO>[OH:12][CH2:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[S:15][CH3:14]

Komponenten

5

Edukt 2

HCID 5557222-Chloro-5-nitrobenzyl alcoholHCID 23662354Mesna

Produkt 1

HCID 223168073-Hydroxymethyl-4-(methylthio)nitrobenzeneAusbeute 105,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-3-(hydroxymethyl)nitrobenzene (20 g, 0.10 mol) in DMSO (160 mL) and MeOH (80 mL), MeSNa (8.2 g, 0.12 mol) was added portionwise at 0° C., and the mixture was stirrred for 2 h at room temperature. The mixture was poured into ice water (300 mL) and the yellow precipitate was collected by filtration and washed with ether (150 mL) gave the title compound (21 g, quantitative).

Aufarbeitung

  1. filtrationthe yellow precipitate was collected by filtration
  2. washwashed with ether (150 mL)

Quellen und Nachweise

ORD-Eintrag
ord-566669d76c614695a16237762494fd90
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608095B2

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