Sodium Hydroxide → 5-Methyl-2-(trifluoromethyl)-3-furancarboxylic acid

HRID 1610326Notes

Reaction equation

HRID 1610326 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]([F:10])([F:9])[F:8])=[C:4]([C:11]([O:13]CC)=[O:12])[CH:3]=1.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]([F:8])([F:9])[F:10])=[C:4]([C:11]([OH:13])=[O:12])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2737208Ethyl 5-methyl-2-(trifluoromethyl)furan-3-carboxylate

Product 1

HCID 27821835-Methyl-2-(trifluoromethyl)-3-furancarboxylic acidYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 45 min
  3. concentrationThe reaction solution was concentrated
  4. additiondiluted with water (150 ml), and 6N hydrochloric acid
  5. additionwas gradually added
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-fe4b792014ad49a490abfa9ccd3cabf8
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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