P-Cresol → Phenyl acetate

HRID 1702426Notes

Reaction equation

HRID 1702426 reaction equation
[C:1]([O:4][CH3:5])(=[O:3])[CH3:2].[CH:6]1[C:11](O)=[CH:10]C=[C:8](C)[CH:7]=1.CI.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C]=O>[Pd](Cl)Cl.C(O)(=O)C>[C:1]([O:4][C:5]1[CH:10]=[CH:11][CH:6]=[CH:7][CH:8]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 2879P-CresolHCID 6328Methyl iodideHCID 6584Methyl AcetateHCID 11776TriphenylphosphineHCID 178418416HCID 178418416, compound

Product 1

HCID 31229Phenyl acetate

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 176Acetic AcidSolvent

Procedure

A 300-ml autoclave equipped with an agitator was charged with 59.2 g of methyl acetate, 104 g of p-cresol, 1.8 g of palladium chloride, 31.5 g of methyl iodide and 5.8 g of triphenylphosphine, and the reaction was carried out at 195° C. and a carbon monoxide pressure of 28 kg/cm2 gauge (total pressure of 38 kg/cm2 gauge). The yields of acetic acid and phenyl acetate were 95.8% and 95.6%, respectively. The reaction was repeated several times, and the resulting reaction product liquids were collected and used in Example 13.

Workup

  1. customA 300-ml autoclave equipped with an agitator
  2. customwas carried out at 195° C.

Sources & evidence

ORD record
ord-0b30621fc61f46bdba933214bc26bda3
Source dataset
uspto-grants-1983_04
Patent number
US04381221

Reaction notes

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