Carbon Tetrachloride → 2-Nitro-3-Methylbenzotrichloride

HRID 1981682Notes

Reaction equation

HRID 1981682 reaction equation
[N+:1]([C:4]1[C:11](C)=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]Br)([O-:3])=[O:2].[OH-].[Na+].[C:15]([Cl:19])(Cl)([Cl:17])[Cl:16]>[Cl-].C([N+](CC)(CC)CC)C.C(Cl)Cl>[N+:1]([C:4]1[C:5]([CH3:6])=[CH:8][CH:9]=[CH:10][C:11]=1[C:15]([Cl:19])([Cl:17])[Cl:16])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 5943Carbon TetrachlorideHCID 14798Sodium HydroxideHCID 129324351-(Bromomethyl)-3-methyl-2-nitrobenzene

Product 1

HCID 135735652-Nitro-3-MethylbenzotrichlorideYield 36%

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

1.5 gms of 2-nitro-3-methyl benzyl bromide was mixed with 0.05 gms of tetraethyl ammonium chloride in 15 ml of methylene chloride and 10 ml of carbon tetrachloride. 20 ml of 50% sodium hydroxide was added and the mixture refluxed for about 3 hours. After completion of the reaction, the organic layer was separated, washed with water, and the product separated to give 36% yield as determined by GC-Mass spectral analysis.

Workup

  1. temperaturethe mixture refluxed for about 3 hours
  2. customAfter completion of the reaction
  3. customthe organic layer was separated
  4. washwashed with water
  5. customthe product separated
  6. customto give 36% yield

Sources & evidence

ORD record
ord-a37bb128ab504e858de531d9a4779775
Source dataset
uspto-grants-1986_06
Patent number
US04593144

Reaction notes

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