Methanol → 2-Chloro-3-(1-cyano-1-methylethyl)benzoic acid

HRID 1800702Notes

Reaction equation

HRID 1800702 reaction equation
[Cl:1][C:2]1[C:11]([C:12]([C:15]#[N:16])([CH3:14])[CH3:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].CO.O.O.[OH-].[Li+]>O1CCCC1>[Cl:1][C:2]1[C:11]([C:12]([C:15]#[N:16])([CH3:14])[CH3:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67312408Methyl 2-chloro-3-(1-cyano-1-methylethyl)benzoate

Product 1

HCID 668102752-Chloro-3-(1-cyano-1-methylethyl)benzoic acidYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-chloro-3-(1-cyano-1-methylethyl)benzoate (1.67 g, 7.02 mmol) in tetrahydrofuran (24 mL)/methanol (8 mL)/water (8 mL) was added lithium hydroxide-monohydrate (501 mg, 11.9 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and 6N hydrochloric acid (2.8 mL) was added dropwise to the residue. The precipitate was collected by filtration, and washed with water to give the title compound (1.43 g, 91%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and 6N hydrochloric acid (2.8 mL)
  2. additionwas added dropwise to the residue
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-30f7642a9cc24c6487e1255607344a51
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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