Sodium Hydroxide → HCID 69795215, compound

HRID 2181661Notes

Reaction equation

HRID 2181661 reaction equation
[CH:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:6]=2[CH:7]=1)=[O:2].[OH:16]P([O-])(O)=O.[K+].[O-]Cl=O.[Na+].[OH-].[Na+]>CS(C)=O.O>[CH3:15][O:14][C:12]([C:10]1[CH:9]=[CH:8][C:6]2[CH:7]=[C:3]([C:1]([OH:16])=[O:2])[O:4][C:5]=2[CH:11]=1)=[O:13]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 516951Monobasic potassium phosphateHCID 22481722588702-95-8HCID 23668197Sodium Chlorite

Product 1

HCID 69795215HCID 69795215, compoundYield 289.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

Methyl 2-formyl-1-benzofuran-6-carboxylate (1.23 g, 6.0 mmol) is dissolved in DMSO (12 ml). KH2PO4 (229 mg, 1.68 mmol) in H2O (2 ml) and NaClO2 (80%, 949 mg, 8.4 mmol) in H2O (12 ml) are added drop-wise to the solution, and the reaction is stirred over the weekend at RT. The pH is adjusted to 10 with 2N NaOH and the mixture is extracted with Et2O (3×50 ml). The pH is adjusted again to 3 with concentrated HCl and the slurry is filtered. The cake is dried overnight, yielding 1.07 g (81%) of 6-(methoxycarbonyl)-1-benzofuran-2-carboxylic acid as an ivory solid. HRMS (FAB) calcd for C11H8O5+H: 221.0450, found 221.0436 (M+H)+.

Workup

  1. extractionthe mixture is extracted with Et2O (3×50 ml)
  2. filtrationthe slurry is filtered
  3. customThe cake is dried overnight

Sources & evidence

ORD record
ord-dfd74f79afd14164b8f2737a18ad798c
Source dataset
uspto-grants-2005_05
Patent number
US06894042B2

Reaction notes

Loading…