Methylene blue cation → HCID 86759450, compound

Participants

Reaction Steps

A solution of 3-[(4′-chloro-[1,1′-biphenyl]-4-yl)-2-butenol (4g, 500 mg) and methylene blue (40 mg) in CH3CN (30 ml) was photooxygenated at 5° C. for 5 h. Cyclohexanone (0.5 ml) and hydrochloric acid (5 drops) were added and reaction mixture was stirred at r.t. for 1.5 h and then left at r.t for 24 h. The reaction mixture was concentrated. Crude product was purified by column chromatography to furnish 360 mg (50% yield, based on allylic alcohol 4g, used) of trioxane 7gb, m.p. 109-111° C.

Provenance & Evidence