Methanol → 3-(2-Cyanopropan-2-yl)benzoic acid

HRID 1874565Notes

Reaction equation

HRID 1874565 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11]C)=[O:10])([CH3:5])[CH3:4])#[N:2].O.[OH-].[Li+].CO.O>O1CCCC1>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([OH:11])=[O:10])([CH3:5])[CH3:4])#[N:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57441035Methyl 3-(2-cyanopropan-2-yl)benzoate

Product 1

HCID 571495383-(2-Cyanopropan-2-yl)benzoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(1-cyano-1-methylethyl)benzoate (2.8 g, 14 mmol) in tetrahydrofuran (30 mL) were added lithium hydroxide monohydrate (0.98 g, 24 mmol), methanol (10 mL) and water (10 mL), and the mixture was stirred at room temperature for 18 hr. The solvent was evaporated under reduced pressure, and the residue was diluted with water (15 mL). 1N Hydrochloric acid was slowly added to adjust the mixture to pH 3. The resulting white precipitate was collected by filtration, washed with water and dried to give the title compound (2.5 g, 98%) as a white powder.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with water (15 mL)
  3. addition1N Hydrochloric acid was slowly added
  4. filtrationThe resulting white precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-94ce6da487974ba0a6ac79ad49c7e844
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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