Methanol → 4-Chloro-3-(1-cyano-1-methylethyl)benzoic acid

HRID 2190474Notes

Reaction equation

HRID 2190474 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[C:12]([C:15]#[N:16])([CH3:14])[CH3:13].CO.O>O1CCCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:12]([C:15]#[N:16])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 67312069Methyl 4-chloro-3-(1-cyano-1-methylethyl)benzoate

Product 1

HCID 668104254-Chloro-3-(1-cyano-1-methylethyl)benzoic acidYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-chloro-3-(1-cyano-1-methylethyl)benzoate (8.0 g, 34 mmol) in tetrahydrofuran (30 mL) were added lithium hydroxide•monohydrate (2.13 g, 51 mmol), methanol (100 mL) and water (5 mL), and the mixture was stirred at room temperature for 4 hr. The solvent was evaporated under reduced pressure, and the residue was diluted with water (200 mL). The mixture was adjusted to pH 3 by slowly adding 1N hydrochloric acid. The resulting white precipitate was collected by filtration, washed with water, and dried to give the title compound (7.40 g, 99%) as a white powder.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with water (200 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-57d7658a14994f9aafa9a61862b562e1
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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