Dimethylformamide → Alpha-chloro-3-methyl-4-nitrotoluene

HRID 1085303Notes

Reaction equation

HRID 1085303 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5]O.CN(C=O)C.S(Cl)([Cl:20])=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5][Cl:20]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 5913603-Methyl-4-nitrobenzyl alcohol

Product 1

HCID 87687Alpha-chloro-3-methyl-4-nitrotoluene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-methyl-4-nitrobenzylalcohol (2 g) and 0.2 ml of DMF were dissolved in 20 ml of toluene. The solution was added with 1 ml of thionyl chloride and stirred under heating with reflux for 3 hours. The reaction mixture was concentrated and thus 2.2 g of an oil, 3-methyl-4-nitrobenzyl chloride, was obtained. This compound was used for the following reaction without further purification.

Workup

  1. temperatureunder heating
  2. temperaturewith reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-76a07a9825f5482d870a479fd38b9eec
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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