Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 9-(2-chloroethyl)-6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one

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Reaction Steps

100 g. (0.5 mole) of 6-methyl-1,2,3,4-tetrahydrocarbazol-1-one and 234.5 g. (1 mole) of p-toluenesulfonic acid-β-chloroethylester are dissolved in 700 ml. of toluene and stirred together with a solution of 4.25 g. (12.5 m moles) of tetrabutylammoniumhydrogensulfate in 500 ml. of aqueous sodium hydroxide solution (30% strength) for 10 hours at room temperature. The organic layer is separated, washed with water and concentrated by evaporation. 108 g. (=83% of the theoretical) of 6-methyl-9-(2-chloroethyl)-1,2,3,4-tetrahydrocarbazol-1-one (melting at 106° to 107° C.) are thus obtained.

Provenance & Evidence