Hydrochloric Acid → 1-(Difluoromethyl)naphthalene-4-carboxylic acid

HRID 1610211Notes

Reaction equation

HRID 1610211 reaction equation
[F:1][CH:2]([F:17])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([O:15]C)=[O:14])=[CH:5][CH:4]=1.[OH-].[Na+].Cl>CO>[F:1][CH:2]([F:17])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22261536Methyl 4-(difluoromethyl)-1-naphthalenecarboxylate

Product 1

HCID 222613881-(Difluoromethyl)naphthalene-4-carboxylic acidYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-(difluoromethyl)-1-naphthalenecarboxylate (450 mg, 1.91 mmol) in methanol (5 ml) was added 2N aqueous sodium hydroxide solution (1.9 ml, 3.8 mmol), and the mixture was stirred overnight at room temperature. 1N Hydrochloric acid was added to the reaction solution (5 ml) and the mixture was extracted with ethyl acetate (20 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give 4-(difluoromethyl)-1-naphthalenecarboxylic acid (344 mg, 81%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (20 ml×2)
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-25c066a2f34d409a846c209adf1c3122
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…