Methanesulfonic Acid → (6R,10R)-6,10,14-trimethylpentadecan-2-one
반응식
[CH3:1][C:2](O)([CH2:5][CH2:6][CH2:7][CH:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[C:3]#[CH:4].C[O:18][C:19]([CH3:21])=[CH2:20].CS(O)(=O)=O.CC([O-])=O.[Na+]>>[CH3:15][C@H:8]([CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:7][CH2:6][CH2:5][C@H:2]([CH2:3][CH2:4][CH2:20][C:19]([CH3:21])=[O:18])[CH3:1]참가 물질
5
실험 절차
44.9 g 3,7,11-trimethyl-1-dodecin-3-ol and 50.5 g isopropenyl methyl ether were initially introduced into a 300 ml V4A steel autoclave with a temperature probe, sampler and pressure indicator. 19 mg methanesulfonic acid were added, while stirring. The autoclave was forced up to 2 bar with nitrogen. The mixture was stirred at 90 to 95° C. for 8 hours. After cooling, the reaction mixture was neutralized with 1.7 ml methanolic NaOAc solution (10 g/1). After evaporation, the crude product was hydrogenated in 2-propanol with 10% Pd/A-charcoal. Phytone was obtained in a yield of 87%.