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Synthesis of 13C-labelled propylene oxide via 13C-labelled 2-chloropropionic acid and 2-chloropropanol

✍ Scribed by Ilan Pri-Bar; Ouri Buchman

Publisher: John Wiley and Sons
Year: 1985
Tongue: French
Weight: 249 KB
Volume: 22
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580221204

No coin nor oath required. For personal study only.

✦ Synopsis

2 -~h l o r o -[ l -~~C ] p r o p i o n y l chloride, phenyl-2-chloro-[l-13Clpropionate, 2-chloro-[ 1-13C] propan-1-01. 1-methyl-[ 2-I3C I ethylene oxide. SUMMARY 13 l-Methyl-[2-Clethylene oxide (I) is prepared in a four-step synthesis, I J starting from [l-Clpropionic acid. A method for an efficient a-chlorination of low carboxylic acids is developed, 2-chloropropionyl chloride being esterified without separation to give 7 2 % of phenyl-2-~hloro-[l-~~C]propionate. The ester is hydrogenated with LiAlH to give 9 5 % yield of 2-chloro-[ l-13Clpropan-l-ol

which is then subjected to alkaline dehydrochlorination, giving 35% yield of the isolated product (I). This micro-scale method is also suitable for syntheses of 14C-labelled epoxides of low molecular weight.

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