Benzoic Acid → Benzyl Benzoate

HRID 651841Notes

Reaction equation

HRID 651841 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](O)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[Pd].C1(C)C=CC=CC=1>[C:1]([O:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 243Benzoic Acid2×HCID 244Benzyl Alcohol2×

Product 1

HCID 2345Benzyl Benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

The oxidation of toluene appears to follow an obvious path as inferred from the kinetics of the product yields (Table IV). The intermediate products are benzyl alcohol, benzaldehyde, benzoic acid; whereas, benzyl benzoate is the final product by esterification of benzyl alcohol and benzoic acid. In a separate test at the same reaction conditions, but without the Pd catalyst, benzyl alcohol and benzoic acid were esterified in toluene to produce benzyl benzoate. The following reaction scheme explains these results:

Workup

  1. customIn a separate test at the same reaction conditions

Sources & evidence

ORD record
ord-090552301cdf41a996cfb45bfad8d69b
Source dataset
uspto-grants-2001_08
Patent number
US06281382B1

Reaction notes

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