Acetic Acid → Phenylacetic Acid

HRID 1903556Notes

Reaction equation

HRID 1903556 reaction equation
[CH2:1](O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.C/C(/[O-])=C/C(C)=O.[C:18]([OH:21])(=[O:20])C>[Ni].O.O.O.O.C([O-])(=O)C.[Ni+2].C([O-])(=O)C.[V].[O-][V]([O-])([O-])=O.[Na+].[Na+].[Na+]>[C:2]1([CH2:1][C:18]([OH:21])=[O:20])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 244Benzyl AlcoholHCID 6328Methyl iodideHCID 5460482Acetylacetonate

Product 1

HCID 999Phenylacetic Acid

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 23990VanadiumCatalystHCID 61671Sodium orthovanadateCatalystHCID 62601Nickel acetate tetrahydrateCatalyst

Procedure

Using the equipment and the procedure described for Example 1, an experiment was carried out on a charge comprising 25 ml (232 mmols) of benzyl alcohol, 15 ml of acetic acid, 161 mmols of methyl iodide, 8 mg atoms of nickel in the form of nickel acetate tetrahydrate and 40 mg atoms of vanadium in the form of vanadyl bis-acetylacetonate. The reaction temperature was 180° C.; the total pressure was maintained at 60 bars by introduction of additional amounts of pure CO. In a reaction time of 1 hour, 30 minutes at the temperature indicated, 15.8 g of phenylacetic acid were obtained (RY=48%).

Workup

  1. customwas 180° C.
  2. temperaturethe total pressure was maintained at 60 bars by introduction of additional amounts of pure CO
  3. customIn a reaction time of 1 hour, 30 minutes

Sources & evidence

ORD record
ord-4d2f53c018084bcf864a994af894fa93
Source dataset
uspto-grants-1984_03
Patent number
US04436889

Reaction notes

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