Lithium hydroxide, monohydrate → 2-Chloro-3-(1-cyanocyclobutyl)benzoic acid

HRID 1800617Notes

Reaction equation

HRID 1800617 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2([C:16]#[N:17])[CH2:15][CH2:14][CH2:13]2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].O.[OH-].[Li+]>O1CCCC1.CO.O>[Cl:1][C:2]1[C:11]([C:12]2([C:16]#[N:17])[CH2:15][CH2:14][CH2:13]2)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68416730HCID 68416730, compound

Product 1

HCID 684190472-Chloro-3-(1-cyanocyclobutyl)benzoic acidYield 65%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-chloro-3-(1-cyanocyclobutyl)benzoate (710 mg, 2.84 mmol) was dissolved in a mixed solvent of tetrahydrofuran (9 mL)/methanol (3 mL)/water (3 mL), lithium hydroxide monohydrate (192 mg, 4.56 mmol) was added, and the mixture was stirred at room temperature for 19 hr. The reaction mixture was concentrated under reduced pressure, and 1N hydrochloric acid (5 mL) was added dropwise to the residue. The precipitate was collected by filtration, and washed with water to give the title compound (435 mg, 65%) as a white powder.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and 1N hydrochloric acid (5 mL)
  3. additionwas added dropwise to the residue
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-3811154acefa47d1a90e5f4413e1aa8a
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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