2,6-Lutidine → 1-Chloro-3-triphenylmethoxyhexane

Participants

Reaction Steps

A stirred solution of 27.3 g. (0.20 moles) of 1-chloro-3-hexanol, 77.6 g. (0.24 moles) of triphenylmethyl bromide, 30,0 g. (0.28 moles of 2,6-lutidine, and 200 ml. of chlorobenzene is heated at 95°C. for 1 hour. The cooled mixture is treated with water, and the organic phase is washed successively with water and saturated sodium chloride solution. The solution is dried over magnesium sulfate and concentrated. Column chromatography of the residue on Florisil affords the subject compound as an oil, ν max. 1600, 1030, and 705 cm-1 (triphenylmethoxy group).

Provenance & Evidence