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

HRID 396811

Reaction equation

HRID 396811 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 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).

Workup

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

Sources & evidence

ORD record
ord-566669d76c614695a16237762494fd90
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Linked notes

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