Hydrochloric Acid → 4-(((1R)-2,2-difluorocyclopropyl)methoxy)benzoic Acid

HRID 2277288Notes

Reaction equation

HRID 2277288 reaction equation
[F:1][C:2]1([F:17])[CH2:4][C@@H:3]1[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][CH:8]=1.C1COCC1.[OH-].[Na+].Cl>CO>[F:1][C:2]1([F:17])[CH2:4][C@@H:3]1[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86731369methyl 4-(((1R)-2,2-difluorocyclopropyl)methoxy)benzoate

Product 1

HCID 867313704-(((1R)-2,2-difluorocyclopropyl)methoxy)benzoic AcidYield 93.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-(((1R)-2,2-difluorocyclopropyl)methoxy)benzoate (637 mg), THF (10 mL), methanol (10 mL) and 1M aqueous sodium hydroxide solution (10 mL) was stirred at room temperature overnight. The reaction mixture was neutralized with 1M hydrochloric acid at 0° C., and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (559 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layer were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-408d12087fb94966a412ce55c2d77d92
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

Loading…