Lauroyl chloride explained

Lauroyl chloride is the organic compound with the formula CH3(CH2)10COCl. It is the acid chloride of lauric acid. Lauroyl chloride is a standard reagent for installing the lauroyl group.[1] It is mainly produced as a precursor to dilauroyl peroxide, which is widely used in free-radical polymerizations.

Lauroyl chloride is a substrate for diverse reactions characteristic of acid chlorides. With base, it converts to laurone, a ketone with the formula [CH<sub>3</sub>(CH<sub>2</sub>)<sub>10</sub>]2CO.[2] With sodium azide, it reacts to give undecyl isocyanate via a Curtius rearrangement of the acyl azide.[3]

References

  1. 10.1016/j.carres.2008.08.023. Rapid homogeneous lauroylation of wheat straw hemicelluloses under mild conditions. 2008. Peng. Feng. Ren. Jun-Li. Peng. Bai. Xu. Feng. Sun. Run-Cang. Sun. Jin-Xia. Carbohydrate Research. 343. 17. 2956–2962. 18793765.
  2. 10.15227/orgsyn.031.0068. Laurone. Organic Syntheses. 1951. 31. 68. J. C. Sauer.
  3. 10.15227/orgsyn.024.0094. Undecyl Isocyanate. C. F. H.. Allen. Alan. Bell. Organic Syntheses. 1944. 24. 94.