Lithium Hydroxide → HCID 21942564, compound

HRID 431867Notes

Reaction equation

HRID 431867 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:13][CH2:14][CH2:15][O:16][CH3:17])[CH:12]=1)[C:6]([O:8]C)=[O:7])#[N:2].[OH-].[Li+]>O1CCCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:13][CH2:14][CH2:15][O:16][CH3:17])[CH:12]=1)[C:6]([OH:8])=[O:7])#[N:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 21942473Benzoic acid, 3-cyano-5-(2-methoxyethoxy)-, methyl ester

Product 1

HCID 21942564HCID 21942564, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of methyl 3-cyano-5-(2-methoxyethoxy)benzoate (375 mg, 1.6 mmol) in tetrahydrofuran (4 mL) was treated with 0.5 N lithium hydroxide (3.8 mL, 1.9 mmol). The reaction was stirred at 70° C. for 30 minutes and then the solvent was removed in vacuo. The residue was dissolved in a small amount of water and then acidified with 2 N hydrogen chloride until pH˜2. Following extraction of the aqueous layer with ethyl acetate, the organic layer washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 343 mg (97%) of 3-cyano-5-(2-methoxyethoxy)benzoic acid.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in a small amount of water
  3. extractionextraction of the aqueous layer with ethyl acetate
  4. washthe organic layer washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2339982827ec4833ada3c421b280bbee
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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