Hydrochloric Acid → 2-Methyl-4-(trifluoromethyl)-3-furancarboxylic acid

Reaction equation

[CH3:1][C:2]1[O:3][CH:4]=[C:5]([C:12]([F:15])([F:14])[F:13])[C:6]=1[C:7]([O:9]CC)=[O:8].C(O)C.[OH-].[Na+].Cl>O>[CH3:1][C:2]1[O:3][CH:4]=[C:5]([C:12]([F:14])([F:13])[F:15])[C:6]=1[C:7]([OH:9])=[O:8]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 14798Sodium Hydroxide

HCID 120093303-Furancarboxylic acid, 2-methyl-4-(trifluoromethyl)-, ethyl ester

Product 1

HCID 218197492-Methyl-4-(trifluoromethyl)-3-furancarboxylic acidYield 90.6%

Reagents, catalysts & solvents 1

Procedure

18 g of the product of Stage B were refluxed for 2 and a half hours in 42 ml of water and 126 ml of ethanol in the presence of 3.55 g of sodium hydroxide. The mixture was allowed to return to room temperature and 2N hydrochloric acid was added to neutrality. The mixture was partially concentrated and 2N sodium hydroxide solution was added. The mixture was extracted with isopropyl ether and the solvent was evaporated to obtain 14.25 g of the expected product melting at 140° C.