Acetic Acid → [(3-Indolyl)(4-methylphenylsulfonyl)]methane

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 5.0 g (0.043 mole) of indole, 1.5 g (0.05 mole) of p-formaldehyde, 7.65 g (0.043 mole) of sodium p-toluenesulfinate, 3.87 ml of glacial acetic acid and 36.6 ml of N,N-dimethylformamide was heated at approximately 150° C. for approximately four hours. The slightly cooled reaction mixture was then slowly poured with stirring into approximately 110 ml of water and 75.0 ml of chlorobenzene was added. The layers were separated after approximately twenty minutes and the water layer extracted a second time with 75.0 ml of fresh chlorobenzene and separated. The organic extracts were combined, washed with cold water and separated. A solid separated and was collected by filtration from the combined chlorobenzene layers and dried to obtain 2.18 g of [(3-indolyl)(4-methylphenylsulfonyl)]methane (Formula X: R=4--CH3 ; R1 =R2 =R3 =R4 =H; n=0) as a white solid which melted at 152°-153° C. developing a dark purple color.

Provenance & Evidence