Lithium hydroxide, monohydrate → HCID 68108300, compound

HRID 385154Notes

Reaction equation

HRID 385154 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:14][C:15]([F:18])([F:17])[F:16])[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]([O:14][C:15]([F:16])([F:17])[F:18])[C:11]=1[O:12][CH3:13])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68108763HCID 68108763, compound

Product 1

HCID 68108300HCID 68108300, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-chloro-4-methoxy-5-trifluoromethoxybenzoate (1.70 g) was dissolved in tetrahydrofuran (12 mL) and water (6 mL), and lithium hydroxide monohydrate (1.00 g) was added to the solution, and the mixture was stirred at room temperature for 2 hours. The solvent was distilled off under reduced pressure and 1N hydrochloric acid was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (1.51 g) as a colorless crystal.

Workup

  1. distillationThe solvent was distilled off under reduced pressure and 1N hydrochloric acid
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d5c89ecb4c58444da216f17bad17386b
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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