Methanesulfonic Acid → HCID 57276568, compound

Participants

Reaction Conditions

Reaction Steps

In a flask equipped with thermometer and reflux condenser, methanol (8.01 g, 250 mmol) and phenylacetylene (6.38 g, 62.5 mmol) were provided and heated to 40° C. Triphenylphosphine gold(I) methyl (14.8 mg, 31.2 μmol) and methanesulfonic acid (40.6 μl, 625 μmol) were then added in rapid succession. After a reaction time of 8 h, 99% of the phenylacetylene had been converted. The main products formed were α-methoxystyrene (selectivity (S)=61%) and acetophenone dimethyl ketal (S=20%). Subsequent acid-catalyzed reaction of the α-methoxystyrene by-produced 1-methoxy-1,3-diphenylbutadiene (as 1:1 cis/trans mixture, S=13%) acetophenone (S=4%) and 1,3,5-triphenylbenzene (S=2%).

Provenance & Evidence