4-Toluenesulfonyl chloride → 1-Tosyl-1H-indole-4-carbaldehyde

Participants

Reaction Steps

150 ml of 50% sodium hydroxide, 4.75 g of tetrabutylammonium hydrogenosulfate and 30.24 g of p-toluene sulfonyl chloride were added to a suspension of 20 g of indole 4-carboxaldehyde in 600 ml of benzene and the mixture was stirred for 90 minutes at ambient temperature. After decanting and extracting with benzene, the extracts were washed with water, dried and evaporated to dryness under reduced pressure. The 42.1 g of residue were dissolved in 210 ml of benzene at reflux, and the solution was allowed to cool to ambient temperature over 16 hours, then separated to obtained 23.96 g of the desired product melting at 144° to 146° C. The product was used as is for the following step.

Provenance & Evidence