Acetic Acid → 2,5-Xylyl acetate

HRID 463626Notes

Reaction equation

HRID 463626 reaction equation
[C:1]1(C)[C:2]([CH3:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:9]([O-:12])(=[O:11])[CH3:10].[K+].[C:14](O)(=O)C>[Pd].O>[C:9]([O:12][C:6]1[CH:1]=[C:2]([CH3:7])[CH:3]=[CH:4][C:5]=1[CH3:14])(=[O:11])[CH3:10]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 7237O-XyleneHCID 517044Potassium Acetate

Product 1

HCID 701412,5-Xylyl acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

xylene, 390 mls of potassium acetate, 0.6 M acetic acid and 0.87 g of palladium catalyst on carbon (10% Pd) are electrolyzed in a cell without diaphragm having a graphite anode (area 140 cm2), steel cathode, magnetic stirrer and water jacket. The electrolysis is carried out at 18° C. with a current of 1.40 A. After the flow of 4 F/mol of electricity, the content of the cell is filtered and extracted with dichloromethane. The organic phase is washed with a solution of NaHCO3 and dried over MgSO4. After having distilled off the solvent under atmospherical pressure, the liquid is transferred into a microdistillation apparatus in which 4.30 g of unreacted p.xylene are recovered together with 3.41 g of pure 2,5-dimethylphenyl acetate. The molar values of the yield of current and the stoichiometric yields relative to the synthesis of 2,5-dimethylphenyl acetate from p.xylene are thus 12.8% and 51.3%, respectively.

Workup

  1. customis carried out at 18° C.
  2. filtrationAfter the flow of 4 F/mol of electricity, the content of the cell is filtered
  3. extractionextracted with dichloromethane
  4. washThe organic phase is washed with a solution of NaHCO3
  5. dry with materialdried over MgSO4
  6. distillationAfter having distilled off the solvent under atmospherical pressure
  7. customxylene are recovered together with 3.41 g of pure 2,5-dimethylphenyl acetate

Sources & evidence

ORD record
ord-736ec41dc581447786cba75e0ef2c710
Source dataset
uspto-grants-1985_10
Patent number
US04544450

Reaction notes

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