HCID 10104617, compound → HCID 10330756, compound

Participants

Reaction Steps

(C15H14O), FW=210.27 g/mol. 1-(1,1-dimethylethyl)-5-phenyl-1,4-pentadiyn-3-ol (5.46 g, 25.6 mmol) was dissolved in dichloromethane (134 mL). Manganese dioxide (13.42 g, 154 mmol) was added and the reaction was heated to reflux for 45 minutes. The reaction mixture was cooled and filtered through celite and concentrated. The orange liquid was obtained in 95% yield. Rf 0.72 (DCM) 1H NMR (500 MHz, CDCl3, ppm) d 7.59 (d, 2H, J=7.3 Hz), 7.46 (t, 1H, J=7.3 Hz), 7.38 (t, 2H, J=7.3 Hz) 1.32 (s, 9H); 13C NMR (75 MHz, CDCl3, ppm) d 161.3, 133.2, 131.0, 128.6, 119.6, 102.6, 90.3, 89.4, 80.8, 29.8, 27.9; HRMS(EI) m/z calculated 210.104465, found 210.103678.

Provenance & Evidence