Lithium hydroxide, monohydrate → HCID 68108929, compound

HRID 385072Notes

Reaction equation

HRID 385072 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([I:15])[C:12]=1[O:13][CH3:14])[C:6]([O:8]C)=[O:7])#[N:2].O.[OH-].[Li+]>O1CCCC1.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([I:15])[C:12]=1[O:13][CH3:14])[C:6]([OH:8])=[O:7])#[N:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68109094HCID 68109094, compound

Product 1

HCID 68108929HCID 68108929, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-cyano-5-iodo-4-methoxybenzoate (8.00 g) was dissolved in tetrahydrofuran (100 mL) and water (50 mL), and lithium hydroxide monohydrate (423 g) was added to the solution, and then the mixture was stirred at room temperature for 4 hours. The organic solvent was distilled off under reduced pressure and the aqueous layer was washed with n-hexane. The aqueous layer was acidified with 2N 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 (7.26 g) as a colorless crystal.

Workup

  1. distillationThe organic solvent was distilled off under reduced pressure
  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-ac9ea6db15354d0495242363ade9a0de
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

Loading…