Sodium Sulfate → HCID 21439768, compound

Participants

Reaction Steps

To a stirred solution of 8.2 g. of lithium aluminum hydride in 180 ml. of tetrahydrofuran was added 40 g. of 2-(4-bromobenzoyl)-benzoic acid in the course of 30 minutes. The mixture, after being kept at 25° for 2 hours, was cooled and 40 ml. of a saturated sodium sulfate solution was added slowly. The mixture was filtered and the filtrate concentrated. The resulting oily residue was dissolved in 32 ml. of acetic acid and 96 ml. of xylene. This solution was added to a mixture of 17.1 g. of selenium dioxide in 60 ml. of acetic acid and 120 ml. of xylene and refluxed for 17 hours. During this time about 22 ml. of an aqueous phase had collected in a Dean Stark receiver. The solution was filtered, washed with sodium hydroxide and concentrated. Addition of petroleum ether gave white prisms melting at 103°-109°. Recrystallization from a mixture of ether and petroleum ether raised the melting point to 110°- 113°. Ultraviolet inflexion (2-propanol) at 225 μ (ε = 17,500) and maximum at 261 μ (ε = 22,200); infrared absorption (CHCl3) at 1675 cm-1 and 1705 cm-1.

Provenance & Evidence