Lithium Hydroxide → HCID 21942503, compound

HRID 431864Notes

Reaction equation

HRID 431864 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:13][CH2:14][CH2:15][CH3:16])[CH:12]=1)[C:6]([O:8]C)=[O:7])#[N:2].[OH-].[Li+]>CO.O1CCCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:13][CH2:14][CH2:15][CH3:16])[CH:12]=1)[C:6]([OH:8])=[O:7])#[N:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 21942451HCID 21942451, compound

Product 1

HCID 21942503HCID 21942503, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of methyl 3-cyano-5-propoxybenzoate (1.5 g, 6.8 mmol) in methanol-tetrahydrofuran (1:2, 30 mL) was treated with 0.5 M lithium hydroxide (16 mL, 8.2 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 (pH˜4) by the addition of 2N hydrogen chloride. The precipitate was collected and dried to afford 1.2 g (86%) of 3-cyano-5-propoxybenzoic acid.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in a small amount of water
  3. additionby the addition of 2N hydrogen chloride
  4. customThe precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-8b8ddd83aa634668a4c2e6e2e39ab987
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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