2‐(1‐Phenylvinyl)benzoic Acid

Molecular skeletal formula with 2 phenyl rings. A central alkene connects them, with a carboxylic acid group on the right ortho position. [17582‐84‐2] C 15 H 12 O 2 (MW 224.08) InChI = 1S/C15H12O2/c1‐11(12‐7‐3‐2‐4‐8‐12)13‐9‐5‐6‐10‐14(13)15(16)17/h2‐10H,1H2,(H,16,17) InChIKey = GUMNEYUSMFGMJT‐UHFFFAOYSA‐N (reagent used for the synthesis of glycosyl ortho ‐(1‐phenylvinyl)benzoates, which could be used as efficient donors in glycosylation reactions) Physical Data: mp 127.7–129.5 °C. Preparative Methods: to a single‐necked, flame‐dried 1000 mL round‐bottomed flask containing a magnetic stir bar, CH 3 PPh 3 Br (31.58 g, 88.41 mmol) was added that had been dried in an oven at 80 °C for 6 h. The flask was sealed with a rubber septum and charged with an argon balloon. Ultra‐dry THF (90% of the total volume, ca 400 mL) was syringed into the flask. The mixture was cooled to 0 °C in an ice bath, and then t ‐BuOK (14.58 g, 132.61 mmol) was slowly added in three portions. After stirring for 30 min, a solution of 2‐benzoylbenzoic acid (10.0 g, 44.20 mmol) in the remaining 10% of ultra‐dry THF (ca 40 mL) was added to the reaction mixture. The temperature was then gradually raised to 80 °C, and the reaction was stirred under reflux for 24 h. After removal of THF by rotary evaporation, the residue was concentrated to afford a yellow solid. Aqueous NaOH (2.5 N, 300 mL) was added, and the mixture was stirred at room temperature for 12 h. The resulting solution was washed with CH 2 Cl 2 three times, and the aqueous layer was acidified with 4 N HCl to pH ≈ 1, then extracted with EtOAc three times. The combined organic layers were dried over Na 2 SO 4 and concentrated to afford ortho ‐(1‐phenylvinyl)benzoic acid as a white solid (9.2 g, 93%). Handling, Storage, and Precautions: 2‐(1‐phenylvinyl)benzoic acid is a stable white solid at room temperature. It is recommended to store it under a dry atmosphere and in a refrigerator.