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

HRID 1597559

Reaction equation

HRID 1597559 reaction equation
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]

Participants

5

Reactant 2

HCID 5557222-Chloro-5-nitrobenzyl alcoholHCID 23662354Mesna

Product 1

HCID 223168073-Hydroxymethyl-4-(methylthio)nitrobenzeneYield 105.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

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 stirred 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).

Workup

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

Sources & evidence

ORD record
ord-7029c23d26d645c7923f1921148939a5
Source dataset
uspto-grants-2001_09
Patent number
US06294558B1

Linked notes

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