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

HRID 1667836Notes

Reaction equation

HRID 1667836 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). The mixture was adjusted to pH 3 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 (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. 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-4e39389e4cfd4b358422571af55a9d19
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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