Toluene → HCID 22151456, compound

Participants

Reaction Steps

To 500 ml of a 5% solution of methyl lithium in ether were added dropwise at room temperature under argon 1200 ml of ether, subsequently 35.6 g of 3,5-lutidine (3,5-dimethylpyridine) and finally 400 ml of toluene. The ether was distilled off completely, whereupon the solution was stirred at 100° for 4 hours. Ice was then added portionwise thereto while cooling with methanol/ice until the evolution of heat no longer occurred. The toluene phase was separated from rhe precipitated solid and was extracted wirh 66 ml of semi-concentrated hydrochloric acid. The separated aqueous phase was adjusted to a pH of about 10 with 3N sodium hydroxide solution while cooling and extracted twice with 300 ml of ether. The ether extracts were dried over sodium sulfate and evaporated. The residue was distilled in vacuo at 20 mm/ 72-74° ; there was obtained 2,3,5-collidine 2,3,5-trimethylpyridine) which had a 99.15% purity in accordance with gas chromatography.

Provenance & Evidence