Water → 2,3-Dihydro-6-hydroxy-4,7-dimethoxybenzofuran-5-carboxylic acid

HRID 21577Notes

Reaction equation

HRID 21577 reaction equation
[OH:1][C:2]1[C:10]([C:11]([OH:13])=[O:12])=[C:9]([O:14][CH3:15])[C:5]2[CH:6]=[CH:7][O:8][C:4]=2[C:3]=1[O:16][CH3:17].O.[OH-].[Na+].[H][H]>C(O)C.[Pd]>[OH:1][C:2]1[C:10]([C:11]([OH:13])=[O:12])=[C:9]([O:14][CH3:15])[C:5]2[CH2:6][CH2:7][O:8][C:4]=2[C:3]=1[O:16][CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 122114615-Benzofurancarboxylic acid, 6-hydroxy-4,7-dimethoxy-HCID 178418361HCID 178418361, compound

Product 1

HCID 199332212,3-Dihydro-6-hydroxy-4,7-dimethoxybenzofuran-5-carboxylic acidYield 73.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5 g of 6-hydroxy-4,7-dimethoxybenzofuran-5-carboxylic acid in 75 ml of ethanol/25 ml of H2O/0.8 g of NaOH are hydrogenated in the presence of 1 g of Pd/C (10%) under atmospheric pressure and at 50° C. until uptake of hydrogen is complete. The mixture is filtered, the ethanol is removed by distillation, the aqueous phase is acidified, and the solid is filtered off with suction. 3.7 g of product are obtained and reacted further without purification.

Workup

  1. filtrationThe mixture is filtered
  2. customthe ethanol is removed by distillation
  3. filtrationthe solid is filtered off with suction

Sources & evidence

ORD record
ord-d4e611dc44724a6b8160f1cb54fb0f2f
Source dataset
uspto-grants-1995_06
Patent number
US05424330

Reaction notes

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