N,N,2-Trimethylaniline → HCID 178506851, compound

Participants

Reaction Steps

A mixture of 96.0 g of N,N-dimethyl-o-toluidine and 444 ml of a 1.6 M solution of butyllithium in hexane was stirred for two days. Stirring was stopped and the orange solution was cooled in ice until it became cloudy, whereupon stirring was resumed with continuing cooling. A yellow solid separated. Volatile materials were removed, about 50 ml of ethyl ether was added, and the solution was stirred for another 24 hours. During this time a large amount of solid separated. It was washed from the flask with pentane to give 2-dimethylaminobenzyllithium in 100% yield (mp above 200° C with decomposition). The infrared absorption spectrum of the product was in agreement with its assigned structure.

Provenance & Evidence