Lithium Hydroxide → HCID 21942607, compound

HRID 2216767Notes

Reaction equation

HRID 2216767 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH2:13][O:14][CH3:15])[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]([CH2:13][O:14][CH3:15])[CH:12]=1)[C:6]([OH:8])=[O:7])#[N:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 21942603HCID 21942603, compound

Product 1

HCID 21942607HCID 21942607, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of methyl 3-cyano-5-(methoxymethyl)benzoate (184 mg, 0.75 mmol) in tetrahydrofuran (2.1 mL) was treated with 0.5 N lithium hydroxide (1.8 mL, 0.90 mmol). The reaction was stirred at 70° C. for 30 minutes and then after cooling 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˜2–3. 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 145 mg (quantitative) of 3-cyano-5-(methoxymethyl)benzoic acid.

Workup

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

Sources & evidence

ORD record
ord-f805ed37f0f74240a9372365bc1dfa58
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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