Thionyl Chloride → 1,5-di-(3,3-dimethylnorborn-2-yl)-3-pentyl Chloride

Participants

Reaction Steps

A solution of 16.6 gm. of 1,5-di-(3,3-dimethylnorborn-2-yl)-3-pentanol in 25 ml. of dry pyridine is cooled to -10° C. There is then added with good agitation, 14.3 gm. of thionyl chloride over a 15 minute period. The solution is allowed to warm to room temperature and gradually heated over a period of 4 to 5 hours to 100° C. After an additional two hours at 100° C. the excess thionyl chloride is removed by vacuum stripping and the reside mixed with cracked ice. Three 100 ml. ether extractions are used to remove the halide, the diethyl ether extracts are washed with 4 × 200 ml. ice water, the ether layer separated, dried over anhydrous magnesium sulfate, filtered and stripped. The residue of di-substituted pentyl chloride may be further purified by distillation in vacuo or is suitable for further reaction as such.

Provenance & Evidence