Lithium hydroxide, monohydrate → HCID 33779593, compound

HRID 385090Notes

Reaction equation

HRID 385090 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([I:14])[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]([I:14])[C:11]=1[O:12][CH3:13])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 33779672HCID 33779672, compound

Product 1

HCID 33779593HCID 33779593, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-chloro-5-iodo-4-methoxybenzoate (2.96 g) was dissolved in tetrahydrofuran (23 mL) and water (7 mL), and lithium hydroxide monohydrate (1.52 g) was added to the solution, and then the mixture was stirred at room temperature for 19 hours. After the organic solvent was distilled off, the mixture was acidified with 1N hydrochloric acid and 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 (2.74 g) as a colorless crystal.

Workup

  1. distillationAfter the organic solvent was distilled off
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f60bed63cb8547bc9955e02f5e52cafd
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

Loading…