Benzoic Acid → Vinyl benzoate

HRID 2295478Notes

Reaction equation

HRID 2295478 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10](OC=C)(=O)[CH3:11].C([O-])(=O)C.[K+]>C(OC=C)(=O)CC.[Cu](Br)Br.O1CCCC1>[C:1]([O:9][CH:10]=[CH2:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 243Benzoic AcidHCID 7904Vinyl AcetateHCID 517044Potassium Acetate

Product 1

HCID 13037Vinyl benzoate

Reagents, catalysts & solvents 3

HCID 7750Vinyl propanoateCatalystHCID 24611Copper bromide (CuBr2)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution consisting of 4.88 g of benzoic acid, 24.8 of vinyl acetate, 0.4 g of potassium acetate, 89.4 mg of copper(II) bromide and 20 ml of tetrahydrofuran was mixed with 1.34 g of the solid catalyst prepared in Example 9. The resulting mixture was heated at 70° C. for 24 hours in the same manner as in Example 9, to form 4.80 g of vinyl benzoate and recover 1.94 g of acetic acid as the byproduct.

Sources & evidence

ORD record
ord-8c0a9837dfdb42b98d2240644c97a5c7
Source dataset
uspto-grants-1984_01
Patent number
US04425277

Reaction notes

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