Lithium Hydroxide → 4-((2,2-Difluorocyclopropyl)methoxy)benzoic acid

HRID 1799260Notes

Reaction equation

HRID 1799260 reaction equation
[F:1][C:2]1([F:17])[CH2:4][CH: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.[OH-].[Li+]>C(O)C>[F:1][C:2]1([F:17])[CH2:4][CH: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

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69020821Methyl 4-[(2,2-difluorocyclopropyl)methoxy]benzoate

Product 1

HCID 690200884-((2,2-Difluorocyclopropyl)methoxy)benzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 4-[(2,2-difluorocyclopropyl)methoxy]benzoate (1.94 g, 8.01 mmol) prepared in Example 40 (40a) was dissolved in ethanol (24 mL), and a 2 M lithium hydroxide aqueous solution (8 mL, 16 mmol) was added thereto at room temperature. The resulting mixture was stirred at the same temperature for 18 hours. The solvents (mainly ethanol) were evaporated, and water was added to the obtained residue. Then, the resulting mixture was changed to weak acidic by adding 2 N hydrochloric acid under ice-cooling with stirring. The precipitated insoluble substance was collected by filtration, washed with water and n-hexane, and dried under reduced pressure to give 1.73 g of the title compound (white powder, yield: 95%).

Workup

  1. customat room temperature
  2. customThe solvents (mainly ethanol) were evaporated
  3. additionwater was added to the obtained residue
  4. additionby adding 2 N hydrochloric acid under ice-
  5. temperaturecooling
  6. stirringwith stirring
  7. filtrationThe precipitated insoluble substance was collected by filtration
  8. washwashed with water and n-hexane
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-2c4307d252044f68be259e76ad5f2114
Source dataset
uspto-grants-2013_01
Patent number
US08344029B2

Reaction notes

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