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

HRID 1654110Notes

Reaction equation

HRID 1654110 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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 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

HCID 962WaterSolvent

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.

Workup

  1. customto return to room temperature
  2. concentrationThe mixture was partially concentrated
  3. addition2N sodium hydroxide solution was added
  4. extractionThe mixture was extracted with isopropyl ether
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-db2556f9bd474c59a44562813949abb7
Source dataset
uspto-grants-1995_04
Patent number
US05405865

Reaction notes

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