Methanol → Methyl 2-(6-hydroxy-1-benzofuran-3-yl)acetate

HRID 922251Notes

Reaction equation

HRID 922251 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:7][O:8][C:4]=2[CH:3]=1.OS(O)(=O)=O.[CH3:20]O>>[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([CH2:9][C:10]([O:12][CH3:20])=[O:11])=[CH:7][O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 21109152-(6-Hydroxy-1-benzofuran-3-yl)acetic acid

Product 1

HCID 20770861Methyl 2-(6-hydroxy-1-benzofuran-3-yl)acetate

Procedure

The obtained crystals of (6-Hydroxy-1-benzofuran-3-yl)acetic acid suspended in methanol (100 mL), and to the suspension was added concentrated H2SO4 (10 mL), and the mixture was stirred at reflux for 4 h. After evaporation of the solvent, the residue was diluted with ether and subsequently washed with water, saturated sodium hydrogen carbonate solution, and brine, dried over anhydrous sodium sulphate and concentrated to give methyl (6-hydroxy-1-benzofuran-3-yl)acetate. The crude material has been purified by column chromatography to obtain the solid (11.23 g, 58%).

Workup

  1. temperatureat reflux for 4 h
  2. customAfter evaporation of the solvent
  3. additionthe residue was diluted with ether
  4. washsubsequently washed with water, saturated sodium hydrogen carbonate solution, and brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7406df783f844f62ab1d3ae99beac31f
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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