Sodium Hydroxide → HCID 57935821, compound

HRID 1434577Notes

Reaction equation

HRID 1434577 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][CH3:14])[C:6]([O:8]C)=[O:7])#[N:2].[OH-].[Na+]>CO.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][CH3:14])[C:6]([OH:8])=[O:7])#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57935767HCID 57935767, compound

Product 1

HCID 57935821HCID 57935821, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 3-cyano-4-ethyl-benzoate (D45) (1.92 g) was dissolved in MeOH (50 mL) before adding 1M NaOH solution (15.24 mL) and stirring the resulting mixture overnight at room temperature, under argon. The reaction mixture was diluted with water, and extracted with EtOAc. The aqueous layer was acidified to pH1 using 2M HCl before extracting with EtOAc. The combined extracts were washed with brine, dried over MgSO4 and the solvent evaporated to dryness in vacuo to afford the title compound (1.63 g). 1H NMR (CDCl3) δ 1.35 (3H, t), 2.97 (2H, q), 7.49 (1H, d), 8.24 (1H, dd), 8.36 (1H, d).

Workup

  1. extractionextracted with EtOAc
  2. extractionbefore extracting with EtOAc
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. customthe solvent evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-9bcb3cfd8019479ca41afac51f31fd03
Source dataset
uspto-grants-2009_11
Patent number
US07615550B2

Reaction notes

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