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

HRID 29380Notes

Reaction equation

HRID 29380 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][CH:18]([CH3:20])[CH3:19])[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][CH:18]([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 687161655-Chloro-4-isopropoxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 687112095-Chloro-4-isopropoxy-3-methyl-benzofuran-2-carboxylic acidYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 110 mg of 5-chloro-4-isopropoxy-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) was added. 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 resulting suspension was filtered. The solid product was dried under vacuum to give 94 mg (94% yield) of 5-chloro-4-isopropoxy-3-methyl-benzofuran-2-carboxylic acid.

Workup

  1. additionwas added
  2. customThe solvents were removed under vacuum
  3. dissolutionthe residue was dissolved in 5 mL of water
  4. customresulting suspension
  5. filtrationwas filtered
  6. customThe solid product was dried under vacuum

Sources & evidence

ORD record
ord-842a1ead2c7b4b30b98906ea20fd9ab6
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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