Benzyl Alcohol → Benzoic Acid

HRID 28186

Reaction equation

HRID 28186 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH2:7]([OH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[OH-].[Na+].[Ru](=O)=O>[C:7]([OH:2])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 23667635Sodium periodate

Product 1

HCID 243Benzoic AcidYield 89%

Reagents, catalysts & solvents 2

HCID 82848Ruthenium dioxideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred suspension of 20 g (94 m mol) sodium periodate in 200 cc of 1 molar sodium hydroxide there was added 0.1 g (0.75 m mol) ruthenium dioxide and 4.32 g (40 m mol) benzyl alcohol. After two hours the reaction was stopped. The mixture was then filtered and the filtrate washed with ether obtaining a neutral fraction comprising benzaldehyde and unreacted benzyl alcohol. The aqueous alkali phase was acidified with sulfuric acid and extracted with ether. There was obtained 4.32 grams of benzoic acid (89% yield).

Workup

  1. filtrationThe mixture was then filtered
  2. washthe filtrate washed with ether obtaining a neutral fraction comprising benzaldehyde and unreacted benzyl alcohol
  3. extractionextracted with ether

Sources & evidence

ORD record
ord-6ede1a92eed94cd3931b64ec1fd29d22
Source dataset
uspto-grants-1980_09
Patent number
US04225694

Linked notes

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