Methanol → 3-(1-Cyanocyclopropyl)benzoic acid

HRID 1663655Notes

Reaction equation

HRID 1663655 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 14 hr. The solvent was evaporated under reduced pressure, and the residue was diluted with water (5.0 mL). The mixture was adjusted to pH 5 by slowly adding 1N hydrochloric acid. The precipitated white precipitate was collected by filtration, washed with water, and air-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. additionby slowly adding 1N hydrochloric acid
  4. filtrationThe precipitated white precipitate was collected by filtration
  5. washwashed with water
  6. customair-dried

Sources & evidence

ORD record
ord-ec038330c89c4c318ede8c26ffb06856
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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