Acetic Acid → Ethyl (E)-3-(4-hydroxy-3-methylbenzofuran-2-yl)propenoate

HRID 978118Notes

Reaction equation

HRID 978118 reaction equation
[OH:1][C:2]1[C:7]2[C:8]([CH3:11])=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14].C(O)(=O)C>O1CCOCC1>[OH:1][C:2]1[C:7]2[C:8]([CH3:11])=[C:9](/[CH:14]=[CH:13]/[C:12]([O:16][CH2:17][CH3:18])=[O:15])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8821Ethyl AcrylateHCID 110080683-Methyl-1-benzofuran-4-ol

Product 1

HCID 13849545Ethyl (E)-3-(4-hydroxy-3-methylbenzofuran-2-yl)propenoateYield 20.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-hydroxy-3-methylbenzofuran (2.9 g, 20 mmoles) palladium III acetate (4.5 g, 20 mmoles), ethyl acrylate (2 g, 20 mmoles), acetic acid (50 ml) and dioxane (200 ml) was refluxed for 3 hours. The mixture was filtered and the filtrate concentrated and chromatographed to obtain 1 g of the title compound after recrystallization from toluene, m.p. 180°-182° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated
  4. customchromatographed

Sources & evidence

ORD record
ord-00559480ef0a4401be948920b4030b28
Source dataset
uspto-grants-1987_05
Patent number
US04663347

Reaction notes

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