Reaction #1697508

Reaction equation

ethyl 5-methyl-2-(trifluoromethyl)-3-furancarboxylate

sodium hydroxide

→

5-methyl-2-(trifluoromethyl)-3-furancarboxylic acid

Yield 94.0%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturethe mixture was heated
2. 2
   Temperatureunder reflux for 45 min
3. 3
   ConcentrationThe reaction solution was concentrated
4. 4
   workup.ADDITIONdiluted with water (150 ml), and 6N hydrochloric acid
5. 5
   workup.ADDITIONwas gradually added
6. 6
   FiltrationThe precipitated crystals were collected by filtration
7. 7
   Washwashed with water

Procedure

To a solution of ethyl 5-methyl-2-(trifluoromethyl)-3-furancarboxylate (25 g, 113 mmol) in ethanol (200 ml) was added 2N aqueous sodium hydroxide solution (61.9 ml, 123.8 mmol) and the mixture was heated under reflux for 45 min. The reaction solution was concentrated, diluted with water (150 ml), and 6N hydrochloric acid was gradually added to adjust to about pH 5. The precipitated crystals were collected by filtration, washed with water to give 5-methyl-2-(trifluoromethyl)-3-furancarboxylic acid (20.5 g, 94%).

Source