Benzyl Alcohol → Benzoic Acid

HRID 1638767Notes

Reaction equation

HRID 1638767 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].C1(CC#N)C=CC=CC=1.[CH2:16]([OH:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.S(=O)(O)[O-:25].[Na+].Cl>O.C1C=CC=CC=1>[C:16]([OH:25])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 5

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 8794PhenylacetonitrileHCID 516875Potassium PermanganateHCID 23665763Sodium Bisulfite

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

Potassium permanganate (3.16 g, 0.02 mol) in water (35 ml) was stirred for 10 minutes and then cooled in a water bath while phenylacetonitrile or benzyl alcohol (0.011 mol), benzene (20 ml) and the catalyst (Table 5) (1mmol) were added. The mixture was stirred for 3 hours at room temperature and worked up by addition of 4% sodium bisulphite (60 ml), acidification with 2N hydrochloric acid, separation of organic layer and extraction of the aqueous layer with benzene (2×20 ml). The combined organic extracts were dried over magnesium sulphate and the solvent evaporated on a rotary evaporator. Recrystallization of the solid residue obtained gives pure benzoic acid.

Workup

  1. additionthe catalyst (Table 5) (1mmol) were added
  2. dry with materialThe combined organic extracts were dried over magnesium sulphate
  3. customthe solvent evaporated on a rotary evaporator
  4. customRecrystallization of the solid residue
  5. customobtained

Sources & evidence

ORD record
ord-cc63c73f754d4a9d866e6dab28a7682e
Source dataset
uspto-grants-1989_11
Patent number
US04880894

Reaction notes

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