Sodium Hydroxide → HCID 57935821, compound

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

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).