Lithium Hydroxide → 5-(trifluoromethyl)benzofuran-2-carboxylic Acid

HRID 2212046Notes

Reaction equation

HRID 2212046 reaction equation
[OH-].[Li+].C([O:5][C:6]([C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[CH:12]=1)=[O:7])C>O.O1CCOCC1.[OH-].[Na+]>[F:19][C:17]([F:18])([F:20])[C:14]1[CH:15]=[CH:16][C:10]2[O:9][C:8]([C:6]([OH:7])=[O:5])=[CH:12][C:11]=2[CH:13]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 21049086Ethyl 5-(trifluoromethyl)benzofuran-2-carboxylate

Product 1

HCID 102361385-(trifluoromethyl)benzofuran-2-carboxylic Acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of lithium hydroxide (78 mg, 3.7 mmol) in water (6 ml) was added to a solution of 5-(trifluoromethyl)benzofuran-2-carboxylic acid ethyl ester (705 mg, 2.73 mmol) in 1,4-dioxane (6 ml). 1,4-Dioxane was added until a clear solution was obtained. The reaction mixture was stirred for 16 h at room temperature. It was diluted with an 1 N aqueous solution of sodium hydroxide and washed with tert-butyl methyl ether (2×30 ml). The aqueous solution was acidified with a 10% aqueous solution of sodium hydrogen sulphate until pH 3 was obtained. It was extracted with ethyl acetate (3×40 ml). The combined ethyl acetate layers were dried over magnesium sulphate. The solvent was removed in vacuo to give crude 5-(trifluoromethyl)benzofuran-2-carboxylic acid which was used in the next step without further purification.

Workup

  1. customwas obtained
  2. washwashed with tert-butyl methyl ether (2×30 ml)
  3. customwas obtained
  4. extractionIt was extracted with ethyl acetate (3×40 ml)
  5. dry with materialThe combined ethyl acetate layers were dried over magnesium sulphate
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6082b062a1e141a7a3b9ec59cc2af4c0
Source dataset
uspto-grants-2006_09
Patent number
US07101898B2

Reaction notes

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