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

HRID 2190461Notes

Reaction equation

HRID 2190461 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>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

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 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-05268ac2ad094d22b6c37e96de2c3fe0
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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