Lithium hydroxide, monohydrate → HCID 68108984, compound

HRID 385055Notes

Reaction equation

HRID 385055 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH2:15][CH3:16])[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]([CH2:15][CH3:16])[C:12]=1[O:13][CH3:14])[C:6]([OH:8])=[O:7])#[N:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68108957HCID 68108957, compound

Product 1

HCID 68108984HCID 68108984, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-cyano-5-ethyl-4-methoxybenzoate (480 mg) was dissolved in tetrahydrofuran (6 mL) and water (2 mL), and lithium hydroxide monohydrate (370 mg) was added to the solution, and then the mixture was stirred at room temperature for 5 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 saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (403 mg) 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 saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2bfbc17d0b33407987042fd375165ecd
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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