Lithium Hydroxide → 4-Propoxy-3-methyl-benzofuran-2-carboxylic acid

HRID 29349Notes

Reaction equation

HRID 29349 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH3:19])[C:9]=2[C:10]=1[CH3:11])=[O:5])C.[Li+].[OH-]>C1COCC1>[CH2:17]([O:16][C:12]1[C:9]2[C:10]([CH3:11])=[C:6]([C:4]([OH:5])=[O:3])[O:7][C:8]=2[CH:15]=[CH:14][CH:13]=1)[CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68712423HCID 68712423, compound

Product 1

HCID 687096234-Propoxy-3-methyl-benzofuran-2-carboxylic acidYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 160 mg of 4-propoxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester dissolved in 1 mL of THF was added 3 mL of LiOH solution (3.6 g LiOH/50 mL MeOH/50 mL H2O). The mixture was stirred at room temperature overnight. The solvents were removed under vacuum and the residue was dissolved in 5 mL of water. The solution was acidified and the resulting suspension was filtered. The solid product was dried under vacuum to give 124 mg (87% yield) of 4-propoxy-3-methyl-benzofuran-2-carboxylic acid, obtained as white solid.

Workup

  1. customThe solvents were removed under vacuum
  2. dissolutionthe residue was dissolved in 5 mL of water
  3. filtrationthe resulting suspension was filtered
  4. customThe solid product was dried under vacuum

Sources & evidence

ORD record
ord-770f199bd7744010ad873ddc1ee33b68
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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