4-Hydroxybenzoic Acid → Ethenyl 4-hydroxybenzoate

HRID 619546Notes

Reaction equation

HRID 619546 reaction equation
[C:1]([O:4][CH:5]=[CH2:6])(=[O:3])[CH3:2].[OH:7][C:8]1[CH:16]=[CH:15]C(C(O)=O)=[CH:10][CH:9]=1.C([O-])(=O)C.[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.ClCCl>[OH:7][C:8]1[CH:16]=[CH:15][C:2]([C:1]([O:4][CH:5]=[CH2:6])=[O:3])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 7904Vinyl AcetateHCID 517044Potassium Acetate

Product 1

HCID 13040874Ethenyl 4-hydroxybenzoateYield 10%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

2000 g of dichloromethane, 24.9 g of vinyl acetate, 40.0 g of 4-hydroxybenzoic acid, 0.79 g of palladium acetate and 3.5 g of potassium acetate were charged into a separable flask of the same type as used in Reference Example 3 and subjected to reaction at 50° C. for 6 hours, while replacing the flask inside atomosphere with a nitrogen gas. After completion of the reaction, the reaction mixture was washed successively with an aqueous 0.5N sodium carbonate solution and water, and then treated in th same manner as in Reference Example 3, whereby 4.8 g of vinyl 4-hydroxybenzoate having the following chemical formula was obtained (yield: 10%): ##STR5##

Workup

  1. customsubjected to reaction at 50° C. for 6 hours
  2. customAfter completion of the reaction
  3. washthe reaction mixture was washed successively with an aqueous 0.5N sodium carbonate solution and water
  4. additiontreated in th same manner as in Reference Example 3, whereby 4.8 g of vinyl 4-hydroxybenzoate having the following chemical formula
  5. customwas obtained (yield: 10%)

Sources & evidence

ORD record
ord-12e3692588a84529baaa0f3f0cbb473a
Source dataset
uspto-grants-1999_09
Patent number
US05959037

Reaction notes

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