Methanol → 2-Chloro-3-(1-cyanocyclopropyl)benzoic acid

HRID 1800654Notes

Reaction equation

HRID 1800654 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2([C:15]#[N:16])[CH2:14][CH2:13]2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].CO.O.O.[OH-].[Li+]>O1CCCC1>[Cl:1][C:2]1[C:11]([C:12]2([C:15]#[N:16])[CH2:14][CH2:13]2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67311674Methyl 2-chloro-3-(1-cyanocyclopropyl)benzoate

Product 1

HCID 668103062-Chloro-3-(1-cyanocyclopropyl)benzoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-chloro-3-(1-cyanocyclopropyl)benzoate (13.5 g, 57.3 mmol) in tetrahydrofuran (180 mL)/methanol (60 mL)/water (60 mL) was added lithium hydroxide monohydrate (3.62 g, 86.3 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and 6N hydrochloric acid (20 mL) was added dropwise to the obtained residue. The precipitate was collected by filtration, and washed with water to give the title compound (11.4 g, 90%) as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and 6N hydrochloric acid (20 mL)
  2. additionwas added dropwise to the obtained residue
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-b849ec5cc14249d0a5abe830e3599f6f
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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