Lithium Hydroxide → 3-Allyloxy-5-cyanobenzoic acid

HRID 431862Notes

Reaction equation

HRID 431862 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([C:15]#[N:16])[CH:14]=1)[C:8]([O:10]C)=[O:9])[CH:2]=[CH2:3].[OH-].[Li+]>CO.O1CCCC1>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([C:15]#[N:16])[CH:14]=1)[C:8]([OH:10])=[O:9])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 21942395Methyl 3-(allyloxy)-5-cyanobenzoate

Product 1

HCID 219425093-Allyloxy-5-cyanobenzoic acidYield 74%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of methyl 3-(allyloxy)-5-cyanobenzoate (1.5 g, 6.9 mmol) in methanol-tetrahydrofuran (1:2, 30 mL) was treated with 0.5 N lithium hydroxide (17 mL, 8.3 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 1.0 g (74%) of 3-allyloxy-5-cyanobenzoic acid as a white solid.

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-008c08ccbe76469fb552fccdceeb17d5
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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