alpha-Chloro-m-nitrotoluene → 1-[(3-Methylbutoxy)methyl]-3-nitrobenzene

HRID 359605

Reaction equation

HRID 359605 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Cl)([O-:3])=[O:2].[CH3:12][CH:13]([CH3:17])[CH2:14][CH2:15][OH:16].[OH-].[K+]>CN(C)C=O>[CH3:12][CH:13]([CH3:17])[CH2:14][CH2:15][O:16][CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

5

Reactant 3

HCID 12078alpha-Chloro-m-nitrotolueneHCID 14797Potassium HydroxideHCID 31260Isoamyl Alcohol

Product 1

HCID 143301471-[(3-Methylbutoxy)methyl]-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

158.1 g (0.92 mol) of 3-nitrobenzyl chloride was dissolved in a mixture of 500 ml (4.59 mol, 5 equivalents) of 3-methyl-1-butanol and 140 ml of dimethylformamide. To the resultant mixture 78 g (1.39 mol, 1.5 equivalents) of KOH pellets were added while the mixture was being cooled in a water bath and stirred strongly. The reaction temperature was elevated to 43° C. and thereafter gradually restored to room temperature. After the mixture was stirred for 7 hours at room temperature, the reaction was completed.

Workup

  1. temperaturewas being cooled in a water bath
  2. customwas elevated to 43° C.
  3. customgradually restored to room temperature
  4. stirringAfter the mixture was stirred for 7 hours at room temperature

Sources & evidence

ORD record
ord-d94e4fb9e1784aa0919f7629290eeb5f
Source dataset
uspto-grants-1991_03
Patent number
US05001275

Linked notes

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