Sodium Hydroxide → 3-Methyl-1-benzofuran-6-carboxylic acid
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- customThe volatiles are removed in vacuo
- dissolutionthe residue is dissolved in H2O (5 ml)
- stirringThe mixture is stirred overnight
- filtrationthe resulting solid is filtered
Sources & evidence
- ORD record
- ord-0b84ab05da874af2a6cbd104e4a749db
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06894042B2
Reaction notes
Loading…