Lithium hydroxide, monohydrate → HCID 33779600, compound

HRID 385024Notes

Reaction equation

HRID 385024 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:14]#[N:15])[C:11]=1[O:12][CH3:13])[C:5]([O:7]C)=[O:6].O.[OH-].[Li+]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:14]#[N:15])[C:11]=1[O:12][CH3:13])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68108614Methyl 3-chloro-5-cyano-4-methoxybenzoate

Product 1

HCID 33779600HCID 33779600, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-chloro-5-cyano-4-methoxybenzoate (1.02 g) was dissolved in tetrahydrofuran (15 mL) and water (6 mL), and lithium hydroxide monohydrate (759 mg) was added to the solution, and then the mixture was stirred at room temperature for 90 minutes. The organic solvent was distilled off and the aqueous layer was washed with n-hexane. The aqueous layer was acidified with 1N hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (946 mg) as a colorless crystal.

Workup

  1. distillationThe organic solvent was distilled off
  2. washthe aqueous layer was washed with n-hexane
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3eaa206d58df4fa5af41816689591f14
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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