Carbon Tetrachloride → Benzene, 1-methyl-3-(trichloromethyl)-

HRID 1981680

Reaction equation

HRID 1981680 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH:5]([Cl:7])[Cl:6].[OH-].[Na+].C(Cl)(Cl)(Cl)[Cl:14]>CCCCCCCCCCCC[N+](C)(C)C.[Cl-]>[CH3:1][C:2]1[CH:3]=[C:4]([C:5]([Cl:14])([Cl:7])[Cl:6])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 14798Sodium HydroxideHCID 5874201-(Dichloromethyl)-3-methylbenzene

Product 1

HCID 599554Benzene, 1-methyl-3-(trichloromethyl)-Yield 101.3%

Reagents, catalysts & solvents 1

HCID 8152Dodecyltrimethylammonium chlorideCatalyst

Procedure

70.0 gms of 3-methyl benzal chloride dissolved in 286.4 gms of carbon tetrachloride was charged into a reaction vessel with 2.67 gms of Aliquat 4 (dodecyltrimethylammonium chloride in alcohol). 192 gms of 50% aqueous sodium hydroxide was added and the mixture heated to reflux for a period of about 4 hours. During this period water was continuously removed from the reaction media using a Dean Stark Trap. After completion of the reaction, the mixture was filtered, water was added to the mixture, and the organic layer was separated by phase separation. The organic layer was stripped on a rotary evaporator to give 84.9 gms of a clear yellow oil. (Yield 93.4%).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for a period of about 4 hours
  3. customDuring this period water was continuously removed from the reaction media
  4. customAfter completion of the reaction
  5. filtrationthe mixture was filtered
  6. additionwater was added to the mixture
  7. customthe organic layer was separated by phase separation
  8. customThe organic layer was stripped on a rotary evaporator

Sources & evidence

ORD record
ord-ccd16b13fb7842e7813ae4946baa47b7
Source dataset
uspto-grants-1986_06
Patent number
US04593144

Linked notes

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