Lithium hydroxide, monohydrate → HCID 68108477, compound

HRID 385060Notes

Reaction equation

HRID 385060 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH:15]2[CH2:17][CH2:16]2)[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]([CH:15]2[CH2:16][CH2:17]2)[C:12]=1[O:13][CH3:14])[C:6]([OH:8])=[O:7])#[N:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68108310Methyl 3-cyano-5-cyclopropyl-4-methoxybenzoate

Product 1

HCID 68108477HCID 68108477, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-cyano-5-cyclopropyl-4-methoxybenzoate (491 mg) was dissolved in tetrahydrofuran (7.5 mL) and water (2.5 mL), and lithium hydroxide monohydrate (359 mg) was added to the solution, and then the mixture was stirred at mom temperature for 20 hours. The organic solvent was distilled off under reduced pressure and the aqueous layer was washed with n-hexane. To the aqueous layer, 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate under acidic conditions. 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 (394 mg) as a pale brown crystal.

Workup

  1. distillationThe organic solvent was distilled off under reduced pressure
  2. washthe aqueous layer was washed with n-hexane
  3. additionTo the aqueous layer, 1N hydrochloric acid was added
  4. extractionthe mixture was extracted with ethyl acetate under acidic conditions
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d3217d6cc8fb41e2aacd9263d1409a95
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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