3-Chloropropanoic acid

Mono-2-alkylation of thianthrene with 2-chloropropanoic acid (74GEP2245940) and dialkylation with phenyltrichloromethane/AlCls (81EGP143901) have been claimed in the patent literature. The unusual 2,6-substitution pattern is claimed for chloromethoxymethylation using ClCH20Me/SnCl4(76IZV2799). 

The names propanoic acid (systematic) and propionic acid (retained) are both approved for the unsubstituted acid. However, the acid CI-CH2-CH2-COOH must be named systematically as 3-chloropropanoic acid. The acid CH3-CH(OH)-COOH is known as lactic acid, if unsubstituted when it is substituted in position 3, for example with chlorine, the name becomes 3-chloro-2-hydroxypropanoic acid. Names such as 3-chloro-2-hydroxypropionic acid or 3-chlorolactic acid are not acceptable. 

S)-2-CHL0R0ALICAII0IC ACIDS OF HIGH EHANTIOMERIC PURITY FROM (S)-2-AMIN0 ACIDS (S)-2-CHLOROPROPANOIC ACID (Propanoic acid, 2-chloro-, (S)-)... 

Sometimes a brownish forerun is observed (bp up to TO C/IO mm for 2-chloropropanoic acid), turning green in a refrigerator and occasionally undergoing vigorous decomposition. It is therefore recommended that distillation be interrupted and the flask containing the forerun removed. 

R.S-iCHLOROPANOlC ACIDS W-CHLOROPROPANOIC ACID S-LACBC ACID... 

Bacterial strains were isolated that could grow on R-CPA [(R)-2-chloropropanoic acid], but not on S-CPA, because although both isomers were dehalogenated by different R and S specific dehalogenase isozymes, the -lactic acid formed from the S-CPA could not be metabolised. 

A wide range of herbicide products exist, all of which require the same (S)-2-chloropropanoic acid precursor, especially the Zeneca Fusilade product. 

Other processes to f S -2-chloropropanoic acid have been developed based on lipase technology, and on fermentation of glucose to -lactic acid and subsequent chemical conversion. 

Whole cells are used in stirred tanks with pH control, producing fS )-2-chloropropanoic acid in 50% yield from the racemate (0.3 M) with an enantiomeric excess of over 95%. This approach was selected in preference to other methods of resolution such as acylation of the racemate and then stereoselective hydrolysis. The dehalogenase enzyme is specific for substrates with a carboxyl group and a 2-chloro or bromo substituent. No cofactor or metal ion is required and reaction involves an inversion of configuration. 

The first few toimes of the (S )-2-chloropropanoic acid were made in 1985-86, and the first production begun in 1987 of 500-1000 ton/a quantities for customers in... 

Reactions possible that are not possible using chemistry. HFCS, cefuroxime, L-tert-leucine, (S)-2-chloropropanoic acid. If -decalactone... 

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