Benzene → 2-Methylbenzoic acid

HRID 2163618Notes

Reaction equation

HRID 2163618 reaction equation
[C:1]1(C)[CH:6]=[CH:5][C:4]([C:7]([OH:9])=[O:8])=[CH:3][CH:2]=1.[Si](Cl)(Cl)(Cl)Cl.Cl.[CH:17]1C=CC=CC=1>>[CH3:17][C:5]1[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 7470P-Toluic AcidHCID 24816Silicon tetrachloride

Product 1

HCID 83732-Methylbenzoic acid

Procedure

To a reaction vessel was added 5 grams (0.037 moles) of para toluic acid suspended in about 100 ml of benzene. Then, 3.14 grams (0.0185 moles) of silicon tetrachloride were added and the reaction mixture stirred at room temperature. A small amount of HCl gas evolved during this stirring. Even though a small amount of material remained undissolved, the reaction mixture was distilled at 80° C. and atmospheric pressure. The overhead condensate contained only benzene and silicon tetrachloride. The pot residue was further heated until p-toluic acid sublimed. Analysis of the liquid remaining in the pot showed it to contain what is probably a silicon chloro toluate.

Workup

  1. distillationthe reaction mixture was distilled at 80° C.
  2. temperatureThe pot residue was further heated until p-toluic acid

Sources & evidence

ORD record
ord-f5619e321d064a44a040df0ae76d662a
Source dataset
uspto-grants-1979_01
Patent number
US04136113

Reaction notes

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