Toluene → HCID 8033815, compound

HRID 745746Notes

Reaction equation

HRID 745746 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]1(=[O:15])[O:14][C:12](=[O:13])[CH2:11][C:9]1=[CH2:10].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[CH3:7][C:1]1[CH:6]=[CH:5][C:4]([C:12]([CH2:11][C:9](=[CH2:10])[C:8]([OH:15])=[O:14])=[O:13])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 75110Itaconic AnhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 8033815HCID 8033815, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 150 ml of methylene chloride were dissolved 35.0 g of toluene and 22.4 g of itaconic anhydride. To this was added gradually 50.0 g of anhydrous aluminum chloride under ice-cooling with stirring, and then the mixture was stirred at room temperature for 5 hours for proceeding the reaction. After completion of the reaction, the reaction solution was concentrated under reduced pressure, poured into a mixture of 40 ml of conc. hydrochloric acid and 500 g of ice, and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. The solvent was evaporated and the residue was recrystallized from a mixture of hexane and ethyl acetate to give 21.6 g of 3-(4-methylbenzoyl)-2-methylenepropionic acid (a compound of formula II wherein X is CH3 and Y is H) (yield: 53%)

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 5 hours
  3. customthe reaction
  4. customAfter completion of the reaction
  5. concentrationthe reaction solution was concentrated under reduced pressure
  6. additionpoured into a mixture of 40 ml of conc. hydrochloric acid and 500 g of ice
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with water
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was evaporated
  11. customthe residue was recrystallized from a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-ef3f1290b023426dbbec03fffbbb07d8
Source dataset
uspto-grants-1986_07
Patent number
US04600540

Reaction notes

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