Benzyl Alcohol → Benzaldehyde

HRID 2259467Notes

Reaction equation

HRID 2259467 reaction equation
[Br-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH:11]O>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.C(O)(=O)C>[CH:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:3]([OH:11])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 244Benzyl Alcohol2×HCID 784Hydrogen PeroxideHCID 253881Sodium Bromide

Product 2

HCID 240BenzaldehydeYield 50.2%HCID 243Benzoic AcidYield 48.8%

Reagents, catalysts & solvents 2

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Cobalt (II) acetate tetrahydrate (0.5 g, 0.002 moles), sodium bromide (0.5 g, 0.005 moles), benzyl alcohol (2.93 g, 0.027 moles) and acetic acid (25 g) were charged to a vessel fitted with a overhead paddle stirrer, thermometer and condenser and heated to 80° C. Hydrogen peroxide (30%, 0.22 moles) was added dropwise down the condenser over two hours during which time the reaction mixture changed colour from deep blue to pink. The reaction was continued for a further 90 minutes after which it was stopped and analysed by HPLC. The analysis revealed that 99.0% of the benzyl alcohol had been consumed, yielding products including benzaldehyde (50.2% yield) and benzoic acid (48.8% yield).

Workup

  1. customfitted with a overhead paddle stirrer
  2. customhad been consumed
  3. customyielding products

Sources & evidence

ORD record
ord-45ad7edd32904de48cfe27fdbae542bf
Source dataset
uspto-grants-1995_12
Patent number
US05473101

Reaction notes

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