Methanol → 3-(1-Cyanocyclopropyl)benzoic acid

HRID 1800421Notes

Reaction equation

HRID 1800421 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). 1N Hydrochloric acid was slowly added to the mixture to adjust the pH to 5. The precipitated 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 precipitated white precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-0383f604c4c54e0ebe7c76aa11a2b13e
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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