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

HRID 1800705Notes

Reaction equation

HRID 1800705 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 to the obtained residue was dropwise added 6N hydrochloric acid (20 mL). 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
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-adc0abffecba4cad91a9a55f75f56335
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

Loading…