Methanol → 3-(1-Cyanocyclopropyl)benzoic acid

HRID 1874573Notes

Reaction equation

HRID 1874573 reaction equation
[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=2)[C:9]([O:11]C)=[O:10])[CH2:5][CH2:4]1)#[N:2].O.[OH-].[Li+].CO.O>O1CCCC1>[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=2)[C:9]([OH:11])=[O:10])[CH2:4][CH2:5]1)#[N:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57441038Methyl 3-(1-cyanocyclopropyl)benzoate

Product 1

HCID 574410393-(1-Cyanocyclopropyl)benzoic acidYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(1-cyanocyclopropyl)benzoate (1.3 g, 6.4 mmol) in tetrahydrofuran (12 mL) were added lithium hydroxide monohydrate (0.44 g, 11 mmol), methanol (4.0 mL) and water (6.0 ml), and the mixture was stirred at room temperature for 4 hr. The solvent was evaporated under reduced pressure, and the residue was diluted with water (5.0 mL). 1N Hydrochloric acid was slowly added to the mixture, and the mixture was adjusted to pH 5. The resulting white precipitate was collected by filtration, washed with water and dried to give the title compound (0.73 g, 61%) as a white powder.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with water (5.0 mL)
  3. addition1N Hydrochloric acid was slowly added to the mixture
  4. filtrationThe resulting white precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-8e5b33af24c24cf5a376373e7f330099
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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