Sodium Hydroxide → (1R,2R)-2-(3,4-Difluorophenyl)cyclopropanecarboxylic acid

HRID 913791Notes

Reaction equation

HRID 913791 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C@@H:11]2[CH2:13][C@H:12]2[C:14]([O:16]CC)=[O:15])[CH:7]=[CH:8][C:9]=1[F:10]>CO>[F:3][C:4]1[CH:5]=[C:6]([C@@H:11]2[CH2:13][C@H:12]2[C:14]([OH:16])=[O:15])[CH:7]=[CH:8][C:9]=1[F:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57407735Ethyl (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylate

Product 1

HCID 9834218(1R,2R)-2-(3,4-Difluorophenyl)cyclopropanecarboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Methanol (322.2 g) and 30% sodium hydroxide aqueous solution (65.5 g, 1.8 molar equivalents) were added to a solution of ethyl (1R,2R)-2-(3,4-difluorophenyl)-1-cyclopropanecarboxylate (48.2 wt % toluene solution, net 61.22 g, 270.6 mmol). The mixture was heated at 65° C. with stirring for 2 hours. The resultant mixture was concentrated under reduced pressure, then toluene and water were added to the concentrate. The mixture was acidified with 35% hydrochloric acid. The organic layer was separated and concentrated under reduced pressure. (1R,2R)-2-(3,4-difluorophenyl)-1-cyclopropanecarboxylic acid was obtained as resultant concentrate (net 52.55 g, yield: 98%).

Workup

  1. concentrationThe resultant mixture was concentrated under reduced pressure
  2. additiontoluene and water were added to the concentrate
  3. customThe organic layer was separated
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cf567b753b7b4610ab2e088b58069324
Source dataset
uspto-grants-2011_09
Patent number
US08026396B2

Reaction notes

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