Lithium Hydroxide → 5-Chloro-4-methoxy-3-methyl-benzofuran-2-carboxylic acid

HRID 29385Notes

Reaction equation

HRID 29385 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([O:17][CH3:18])[C:9]=2[C:10]=1[CH3:11])=[O:5])C.[Li+].[OH-]>C1COCC1>[Cl:16][C:13]1[CH:14]=[CH:15][C:8]2[O:7][C:6]([C:4]([OH:5])=[O:3])=[C:10]([CH3:11])[C:9]=2[C:12]=1[O:17][CH3:18]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 687120345-Chloro-4-methoxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 687142675-Chloro-4-methoxy-3-methyl-benzofuran-2-carboxylic acidYield 87.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 105 mg of 5-chloro-4-methoxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester was added 1 mL of THF and 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 triturated with dichloromethane and dried under vacuum to give 82 mg (87% yield) of 5-chloro-4-methoxy-3-methyl-benzofuran-2-carboxylic acid.

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 triturated with dichloromethane
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ada43d0ea24542d0ab8535f1ba6c361d
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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