Sodium Hydroxide → 3-Methyl-1-benzofuran-6-carboxylic acid

HRID 2181672Notes

Reaction equation

HRID 2181672 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([O:13]C)=[O:12])=[CH:10][C:5]=2[O:4][CH:3]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:5]=2[O:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22481752Methyl 3-methyl-1-benzofuran-6-carboxylate

Product 1

HCID 693624603-Methyl-1-benzofuran-6-carboxylic acidYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-methyl-1-benzofuran-6-carboxylate (720 mg, 3.78 mmol) is dissolved in MeOH (10 ml), treated with 2N NaOH (2.27 ml, 4.5 mmol) and stirred overnight. The volatiles are removed in vacuo, the residue is dissolved in H2O (5 ml) and the pH is adjusted to 3 with concentrated HCl. The mixture is stirred overnight and the resulting solid is filtered to afford 545 mg (82%) of 3-methyl-1-benzofuran-6-carboxylic acid as a white solid. HRMS (FAB) calcd for C10H8O3+H: 177.0552, found 177.0551 (M+H)+.

Workup

  1. customThe volatiles are removed in vacuo
  2. dissolutionthe residue is dissolved in H2O (5 ml)
  3. stirringThe mixture is stirred overnight
  4. filtrationthe resulting solid is filtered

Sources & evidence

ORD record
ord-0b84ab05da874af2a6cbd104e4a749db
Source dataset
uspto-grants-2005_05
Patent number
US06894042B2

Reaction notes

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