Methanol → Methyl 2,3-dihydrobenzofuran-7-carboxylate

HRID 1162069Notes

Reaction equation

HRID 1162069 reaction equation
[O:1]1[C:5]2[C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[CH3:13]O.S(=O)(=O)(O)O>>[O:1]1[C:5]2[C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27950142,3-Dihydro-1-benzofuran-7-carboxylic acid

Product 1

HCID 15062252Methyl 2,3-dihydrobenzofuran-7-carboxylate

Conditions

Temperature
80 °C

Procedure

2,3-Dihydrobenzofuran-7-carboxylic acid (8 g, 48.7 mmol) was dissolved in methanol (39.6 mL, 975 mmol) and concentrated sulfuric acid (2.6 mL, 48.7 mmol) was slowly added. The mixture was refluxed at 80° C. for 17 h. The solvent was evaporated and the residue was dissolved in ethyl acetate and washed with brine. The organic layer was evaporated to give the title compound as a beige solid. Yield: 8.6 g (99%). HPLC purity 93%, RT=1.72 min (System A; 10-97% MeCN over 3 min); 96%, RT=1.67 min (System B; 10-97% MeCN over 3 min). MS (ESI+) for C10H10O3 m/z 179 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with brine
  4. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-84e138e4c4bd4b6991d08019854de940
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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