Methylene blue cation → Benzofuran

Participants

Reaction Conditions

Reaction Steps

Under the condition of 25° C. and 1 atmospheric pressure, 5.2 mg of 3-[1-(2-hydroxy-4,6-dimethoxyphenyl)-3-methylbutylthio] propanoic acid and 7.2 mg of α-phellandrene were added to the solvent system consisting of of 5 mL of cyclohexane, 4 mL of nitroethane and 1 mL of nitromethane contained in a pyrex glass container and dissolved. Further, 264 mg of lithium perchloride (acceleration of carbon-sulfur cleavage reaction along with the photo electron transportation of a sulfur atom progressed by light irradiation to methylene blue and acceleration of inner molecular ring forming reaction) and 2.3 mg of methylene blue were added and dissolved completely. Lithium perchloride and methylene blue were completely dissolved in the lower layer (nitroalkane layer). By heating this solution to 55° C., homogenized completely and under the argon gas flow halogen lamp (visible ray lamp, wave length from 400 nm to 700 nm) was irradiated for 4 hours. After irradiation, by cooling the reaction solution to 25° C., phase separation occurred again (separated solution system). In the lower layer, methylene blue, lithium perchloride, disulfide generated along with the progress of the reaction and un-reacted starting materials were refined. And, in the cyclohexane layer, the reacted product is refined. Yield is 53%.

Provenance & Evidence