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Synthesis of 6-Bromohexanoic Acid

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Published on Dec 18, 2011

6-Bromohexanoic acid is prepared in a two step process from readily available polycaprolactone plastic. Heating with aqueous NaOH affords sodium 6-hydroxyhexanoate and sodium salts of short chain oligomers. Reaction with HCl and removal of the NaCl using an acetone precipitation affords a soluble mixture of 6-hydroxyhexanoic acid and oligomers that are then reacted with azeotropic HBr using a H2SO4 catalyst (per Orgsyn Vol 1, pg 3) to afford 6-bromohexanoic acid, which is purified by vacuum distillation. Yield is 54.4% of a crystalline product melting from 28-32C, indicating some slight impurities (literature m.p. 32-34C). The intro music clip is from "Stealing Fat" by The Dust Brothers. I believe this falls under fair use.

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