Phenylacetic Acid → 3-(4-tert-Butyl-phenyl)-2-phenyl-acrylic Acid

反応式

[C:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].C(OC(=O)C)(=O)C>Cl>[C:11]([C:15]1[CH:16]=[CH:17][C:18]([CH:19]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]([OH:10])=[O:9])=[CH:21][CH:22]=1)([CH3:14])([CH3:13])[CH3:12]

参加物

実験手順

Phenyl acetic acid (489 mg, 3.59 mmol) and 4-t-butylbenzaldehyde (573 mmg, 3.53 mmol), TEA (5 ml) and acetic anhydride (5 ml) were added in round flask. A reaction mixture was heated and stirred overnight. The reaction mixture was poured into 5% HCl aqueous solution (30 ml). A aqueous solution was extracted with MC (30 ml×3). A combined organic layer was dried over MgSO4 and then concentrated in vacuo. The crude residue was column-chromatographed (hexane/ethylacetate=4/1) to yield a white solid (382 mg, 73%)