Water → Methyl 3-(benzofuran-4-yl)benzoate

HRID 1740292Notes

Reaction equation

HRID 1740292 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]3[CH:11]=[C:12]([C:16]4[O:17][CH2:18]C(C)(C)N=4)[CH:13]=[CH:14][CH:15]=3)[C:4]=2[CH:3]=[CH:2]1.S(=O)(=O)(O)[OH:24].O>CO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]3[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=3)[C:16]([O:17][CH3:18])=[O:24])[C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 218382442-[3-(Benzofuran-4-yl)phenyl]-4,4-dimethyl-4,5-dihydrooxazole

Product 1

HCID 21838203Methyl 3-(benzofuran-4-yl)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-[3-(benzofuran-4-yl)phenyl]-4,4-dimethyl-4,5-dihydrooxazole (1.4 g), concentrated sulfuric acid (0.8 ml) and water (1 ml) in methanol (20 ml) was refluxed for 48 hours. After evaporating the solvent, the residue was dissolved in a mixture of ethyl acetate (50 ml) and water (50 ml). The organic layer was successively washed with 10% sodium carbonate aqueous solution, brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with toluene. The fractions containing the desired products were collected and evaporated in vacuo to afford methyl 3-(benzofuran-4-yl)benzoate (0.77 g).

Workup

  1. temperaturewas refluxed for 48 hours
  2. customAfter evaporating the solvent
  3. dissolutionthe residue was dissolved in a mixture of ethyl acetate (50 ml) and water (50 ml)
  4. washThe organic layer was successively washed with 10% sodium carbonate aqueous solution, brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was purified by column chromatography on silica gel eluting with toluene
  8. additionThe fractions containing the desired products
  9. customwere collected
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-7d8abc6380b548e4b1101183b65eb383
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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