Sodium Hydroxide → 3-(4-Cyano-3-hydroxy-phenyl)-propionic acid

Reaction equation

C([O:3][C:4](=[O:16])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([OH:15])[CH:8]=1)C.[OH-].[Na+]>C(O)C.O>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][C:4]([OH:16])=[O:3])=[CH:8][C:9]=1[OH:15])#[N:14]

Participants

Procedure

A solution of 3-(4-Cyano-3-hydroxy-phenyl)-propionic acid ethyl ester (2.2 g, 10 mmol) in ethanol (10 mL) and water (40 mL) was treated with aqueous sodium hydroxide solution (2.5 M, 44 mL) at room temperature overnight. The solvent was removed under vacuum and the residue was dissolved in water (150 mL). The pH of the aqueous solution was adjusted to 2–4 by the addition of 3N HCl (aqueous) and the precipitate was then filtered and washed with water to give the title compound as white solid (1.88 g, 0.98 mmol, 98.4% yield). ESMS m/z: 192 [M+H]+.