Benzyl Alcohol → Benzoic Acid

HRID 1829961Notes

Reaction equation

HRID 1829961 reaction equation
Br([O-])(=O)=O.[Na+].[CH2:6]([OH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CC[O:16]CC>C(#N)C.O>[C:6]([OH:16])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 3283Diethyl EtherHCID 23668195Sodium Bromate

Product 1

HCID 243Benzoic AcidYield 90%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

A mixture of Ceiv catalyst from EXAMPLE 47 (0.08 g), sodium bromate (0.3 g) and benzyl alcohol (0.216 g, 2 mmol) in acetonitrile:water (5:7, 12 ml) was stirred at 80° C. for 40 h under an atmosphere of nitrogen. On cooling ether (70 ml) was added and the catalyst was filtered off. The organic layer was separated and the aqueous phase was extracted with ether (2×50 ml). The combined organic extracts were washed with water (25 ml), dried with anhydrous magnesium sulphate and concentrated to give benzoic acid as a white solid (0.22 g, 90%). M.p. 120° C., lit. 120–122° C.

Workup

  1. additionwas added
  2. filtrationthe catalyst was filtered off
  3. customThe organic layer was separated
  4. extractionthe aqueous phase was extracted with ether (2×50 ml)
  5. washThe combined organic extracts were washed with water (25 ml)
  6. dry with materialdried with anhydrous magnesium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-03e218dc4dde46598f1d8ba4bfa5865d
Source dataset
uspto-grants-2006_06
Patent number
US07064226B2

Reaction notes

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