Methanol → 3-(1-Cyanocyclopropyl)benzoic acid

HRID 2190491Notes

Reaction equation

HRID 2190491 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].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

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 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 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. additionby slowly adding 1N hydrochloric acid
  4. filtrationThe resulting white precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-7e57846fc40f4d7bb2b14dad3bd3466f
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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