Sulfuric Acid → HCID 13276468, compound

Participants

Reaction Steps

To a solution of 8.7 g (45 mmoles) of p-toluenesulfonyl chloride in 60 ml pyridine was added dropwise at 0°-5° C., a solution of 5.8 g (31.8 mmoles) of (Z,Z)-3,6-dodecadienol (T. Kajiwara, J. Sekiya, Y. Odake and A. Hatanaka, Agric. Biol. Chem., 41, 1481 (1977)). The temperature was allowed to rise to 25° C., and the reaction mixture was stirred at room temperature overnight. The resulting suspension was slowly poured into a mixture of 1 N aqueous sulfuric acid and ice and the product extracted with ether. The ether extracts were combined, washed with 10% sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent evaporated under reduced pressure. The residue (8.0 g) was chromatographed on a silica gel column. Elution with 1:1 hexane-ether gave 4.9 g (14.6 mmoles) (45.8%) of (Z,Z)-3,6-dodecadienyl tosylate, which was dissolved in 20 ml of acetone.

Provenance & Evidence