Methanol → Methyl 5-hydroxybenzofuran-2-carboxylate

HRID 1947467Notes

Reaction equation

HRID 1947467 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([OH:12])=[O:11])=[CH:7][C:6]=2[CH:13]=1.S(=O)(=O)(O)O.[CH3:19]O>>[CH3:19][O:11][C:10]([C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:13][C:6]=2[CH:7]=1)=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 122089725-Hydroxybenzofuran-2-carboxylic acid

Product 1

HCID 12208973Methyl 5-hydroxybenzofuran-2-carboxylateYield 83%

Procedure

To a solution of 5-hydroxy-benzofuran-2-carboxylic acid (4.6 g, 26.0 mmol) in MeOH (100 mL) was added concentrated sulfuric acid (1.2 g, 13.0 mmol) and the resultant solution was heated (reflux, 18 h). The reaction was cooled (rt) and concentrated in vacuo. The resultant residue was purified by silica gel flash column chromatography using MeOH:DCM (10%) to provide the title compound (4.14 g, 83%). MS (ESI): mass calcd for C10H8O4, 192.0; m/z found, 193.1 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.47 (s, 1H), 7.39 (d, J=9.0, 1H), 7.04 (d, J=2.5, 1H), 6.97 (dd, J=9.0, 2.5, 1H), 3.92 (s, 3H).

Workup

  1. temperature(reflux, 18 h)
  2. concentrationconcentrated in vacuo
  3. customThe resultant residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-f48aca3efcba4a49be61d06c12167734
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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