Methanol → HCID 67812897, compound

HRID 591538Notes

Reaction equation

HRID 591538 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[C:3]=1[CH3:15].OS(O)(=O)=O.[CH3:21]O>>[CH3:21][O:11][C:10](=[O:12])[CH2:9][C:6]1[C:5]2[CH:13]=[CH:14][C:2]([OH:1])=[C:3]([CH3:15])[C:4]=2[O:8][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 4738325HCID 4738325, compound

Product 1

HCID 67812897HCID 67812897, compound

Conditions

Temperature
60 °C

Procedure

To a mixture of (6-hydroxy-7-methyl-1-benzofuran-3-yl)acetic acid (2.61 g) in MeOH (80 mL) was added conc. H2SO4 (0.135 mL). The mixture was stirred at 60° C. for 1 h. The mixture was concentrated. The mixture was neutralized with saturated aqueous NaHCO3 and extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (2.52 g).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-dfeed80a6ae941e9a553be9e9ea1a313
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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