Carbon Tetrachloride → 2-(Trichloromethyl)benzoyl chloride

HRID 1659828Notes

Reaction equation

HRID 1659828 reaction equation
[C:1]1(C)[C:2]([C:7]([Cl:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.ClCl.[C:13]([Cl:17])(Cl)([Cl:15])[Cl:14]>>[Cl:14][C:13]([Cl:17])([Cl:15])[C:1]1[C:2]([C:7]([Cl:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 5943Carbon Tetrachloride2×HCID 24526ChlorineHCID 702762-Methylbenzoyl chloride

Product 1

HCID 30167522-(Trichloromethyl)benzoyl chlorideYield 80%

Procedure

Five g (0.032 mole) of o-toluic chloride was dissolved in 150 ml of carbon tetrachloride and reaction was carried by passing dry chlorine into the solution under irradiation with an ultraviolet lamp while refluxing carbon tetrachloride. From the reaction mass an amount thereof necessary for gas chromatographic analysis was occasionally withdrawn to examine the change of the peak of α,α-dichloro-o-toluic chloride by comparing with an authentic sample, the introduction of chlorine was stopped after the peak was disappeared. Part of the oily matter obtained by reduced pressure distillation for removal of carbon tetrachloride was withdrawn, and on analyzing it by gas chromatography it was possible to ascertain that 1,1,3,3-tetrachloro-1,3-dihydroisobenzofuran and α,α,α-trichloro-o-toluic chloride was formed in a mixed ratio by weight of about 6:4, yield 6.6 g (chlorination yield 80%).

Workup

  1. customreaction
  2. customunder irradiation with an ultraviolet lamp
  3. customFrom the reaction mass an amount thereof necessary for gas chromatographic analysis was occasionally withdrawn
  4. customPart of the oily matter obtained by reduced pressure distillation for removal of carbon tetrachloride
  5. customwas withdrawn

Sources & evidence

ORD record
ord-265a1100f16941c0b20495927d86cd76
Source dataset
uspto-grants-1981_12
Patent number
US04305889

Reaction notes

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