Toluene → HCID 19833512, compound

HRID 2051389Notes

Reaction equation

HRID 2051389 reaction equation
[C:1]1(C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:8][C:9]([F:15])([F:14])S(O)(=O)=O.F[C:17]([C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23])(F)F>CCCCCC>[F:8][C:9]([F:15])([F:14])[C:1]1[CH:6]=[CH:5][C:4]([C:22]([C:21]2[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=2[CH3:17])=[O:23])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 62406Trifluoromethanesulfonic acidHCID 675612-(Trifluoromethyl)benzoyl chloride

Product 1

HCID 19833512HCID 19833512, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
110 °C

Procedure

In a glass reactor, a mixture of 600 ml of toluene and 22.5 g of trifluoromethanesulfonic acid were kept heated at 110° C., and, while stirring the mixture, 312.8 g of trifluoromethylbenzoyl chloride was dropped into the reactor so as to spend 5 hr in dropping the entire quantity. After that the heating and stirring were continued for 5 hr, and then 1.2 liter of hexane was added to cause precipitation of 4-trifluoromethyl-4'-methylbenzophenone in the form of platy crystals. The cystalline precipitate was collected by filtration, washed and dried. The dried product weighed 276 g (69% yield). From the filtrate, 111 g (28% yield) of 4-trifluoromethyl-2'-methylbenzophenone was obtained.

Workup

  1. additionwas dropped into the reactor so as
  2. waitwere continued for 5 hr
  3. customprecipitation of 4-trifluoromethyl-4'-methylbenzophenone in the form of platy crystals
  4. filtrationThe cystalline precipitate was collected by filtration
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-251f1f60c80b4f3580b12592eb592189
Source dataset
uspto-grants-1991_05
Patent number
US05017730

Reaction notes

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