Benzene → HCID 86750973, compound

Participants

Reaction Steps

1-(3,5-dimethoxy-4-hydroxyphenyl-1,2-ethanedithiol (40) (2.46 g, 10.0 mmole), 3,5-dimethoxy-4-hydroxybenzaldehyde (indicated as arylaldehyde E in FIG. 1) (1.32 g, 7.20 mmole) and 1.00 g of pyridinium paratoluene sulfonate are added to 50 ml dry benzene and refluxed with Dean-Stark removal of the benzene-water azeotrope overnight. The benzene is removed in vacuo, and the remaining oil redissolved in dichloromethane. The organic layer is washed with 10% NaHCO3 and H2O. The organic layer is dried over MgSO4, filtered, and evaporated in vacuo to a white solid which is recrystallized from methanol (2.510 g, 85%). The trans isomer (0.683 g) is isolated by recrystallization from methanol. NMR: (CDCl3) 3.45,dd,1H;3.61,dd,1H; 3.91,s,6H;3.92,s,6H;5.07,dd,1H;5.50,d,2H;5.83,s,1H; 6.73,s,2H;6.84,s,2H. M.S.: (CI) 411 (100%). Melting Point: 169°-170° C. C,H,S Analysis: (theoretical, actual) C (55.59,55.58); H (5.40,5.44); S (15.62,15.56).

Provenance & Evidence