2-Chloropropionic acid

This colorless liquid is the simplest chiral chlorocarboxylic acid, and it is noteworthy for being readily available as a single enantiomer.

Reduction of (S)-2-chloropropionic acid with lithium aluminium hydride affords (S)-2-chloropropanol, the simplest chiral chloro-alcohol.

This alcohol undergoes cyclization upon treatment with potassium hydroxide, which causes dehydrohalogenation to give the epoxide, (R)-propylene oxide (methyloxirane).

[3] 2-Chloropropionyl chloride reacts with isobutylbenzene to give, after hydrolysis, ibuprofen.

[1] In general, α-halocarboxylic acids and their esters are good alkylating agents and should be handled with care.

2-Chloropropionic acid
2-Chloropropionic acid