Methanol → HCID 68502921, compound

HRID 1712343Notes

Reaction equation

HRID 1712343 reaction equation
[CH3:1][C:2]1[C:10]2[O:9][C:8]([C:11]([OH:13])=[O:12])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:14]O>OS(O)(=O)=O>[CH3:1][C:2]1[C:10]2[O:9][C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 203039687-Methyl-1-benzofuran-2-carboxylic acid

Product 1

HCID 68502921HCID 68502921, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 4.32 g of 7-methylbenzofuran-2-carboxylic acid in 150 ml of methanol and 1 ml of conc. H2SO4 is stirred at reflux over 9 hours. The reaction mixture is cooled and concentrated by evaporation. The residue is dissolved in diethyl ether and washed with water, saturated aqueous sodium hydrogencarbonate solution and brine, dried over sodium sulphate and concentrated by evaporation. The crude title compound is obtained as a red-brown oil from the residue. Rf=0.32 (1:6 EtOAc-heptane); Rt=4.51.

Workup

  1. temperatureat reflux over 9 hours
  2. temperatureThe reaction mixture is cooled
  3. concentrationconcentrated by evaporation
  4. dissolutionThe residue is dissolved in diethyl ether
  5. washwashed with water, saturated aqueous sodium hydrogencarbonate solution and brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-7bc790785fd94aeebdabcc5e59cea713
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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