Sodium Hydroxide → 3-Methyl-1-benzofuran-5-carboxylic acid

HRID 2181675Notes

Reaction equation

HRID 2181675 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([C:11]([O:13]C)=[O:12])[CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1.[OH-].[Na+]>CO.O>[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 111714895-Benzofurancarboxylic acid, 3-methyl-, methyl ester

Product 1

HCID 228321223-Methyl-1-benzofuran-5-carboxylic acidYield 95.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Methyl 3-methyl-1-benzofuran-5-carboxylate (365 mg, 1.9 mmol) is dissolved in MeOH (7 mL), diluted with H2O (3.5 mL) and treated with 3N NaOH (1.41 mL, 4.2 mmol). The mixture is diluted with MeOH (3.5 mL) to homogeneity, stirred at RT for 2.5 days then concentrated to dryness. The residue is dissolved in H2O (5 mL) and acidified to pH 2 with concentrated HCl. The resulting solid is filtered and dried in a vacuum oven at 40° C. for 18 h to afford 321 mg (95%) of 3-methyl-1-benzofuran-5-carboxylic acid as a white solid. HRMS (FAB) calcd for C10H8O3+H: 177.0552, found: 177.0553 (M+H)+.

Workup

  1. concentrationthen concentrated to dryness
  2. dissolutionThe residue is dissolved in H2O (5 mL)
  3. filtrationThe resulting solid is filtered
  4. customdried in a vacuum oven at 40° C. for 18 h

Sources & evidence

ORD record
ord-379062f285a94a91a6b87e4c0ba0ca87
Source dataset
uspto-grants-2005_05
Patent number
US06894042B2

Reaction notes

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