Acetaldehyde → [(Methyl)(1-ethyl-2-methyl-3-indolyl)(4-methylphenylsulfonyl)]methane

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 175.0 ml of ethyl alcohol, 30.35 g (0.14 mole) of 81.4 percent sodium p-toluenesulfinate, 19.5 g (0.112 mole) of 91.2 percent 1-ethyl-2-methylindole and 5.5 g (0.125 mole) of acetaldehyde under an atmosphere of nitrogen and maintaining the temperature at approximately 5° C. by means of an ice-water bath, there was added dropwise 27.5 ml of concentrated hydrochloric acid. After stirring approximately four hours at ambient temperature, the white solid which had separated was collected by filtration, washed with a small amount of ethyl alcohol and air dried to a constant weight of 43.7 g. The solid was dissolved in a hot mixture of ethyl and methyl alcohols, treated with 3.0 g of decolorizing charcoal, the solution filtered while hot, and then set aside at ambient temperature overnight. The resulting slurry was placed in a refrigerator for approximately two hours. The separated solid was then collected by filtration, washed with 500.0 ml of ethyl alcohol and air-dried to obtain 17.8 g of [(methyl)(1-ethyl-2-methyl-3-indolyl)(4-methylphenylsulfonyl)]methane (Formula X: R=4--CH3 ; R1 =C2H5 ; R2 =CH3 ; R3 =R4 =H; n=1), a pale yellow solid which melted at 140°-142° C. developing a purple color.

Provenance & Evidence