Process for the preparation of an alkyl 2-chloropropionate by ch

Details Process for the preparation of an alkyl 2-chloropropionate by ch Process for the preparation of an alkyl 2-chloropropionate by ch

1980-05-21

1982-06-08

Killos, Paul J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

560150, C07C 6963

Patent

active

043340830

ABSTRACT:
A racemic or optically active alkyl 2-chloropropionate is prepared, respectively, from a racemic or optically active alkyl lactate by, in a first step, gradually bringing the alkyl lactate into contact with the thionyl chloride, in the presence of an organic base, while maintaining, in the reaction mixture, an excess of thionyl chloride, relative to the amount of alkyl lactate introduced into this mixture, at a temperature below the decomposition point of the chlorosulphinate of the alkyl lactate, which is formed as an intermediate, and then, in a second step, in heating the reaction mixture resulting from the first step at a temperature which is at least equal to the decomposition point of the chlorosulphinate of the alkyl lactate.
The alkyl 2-chloropropionates can be used for the manufacture of the racemic or optically active 2-phenoxypropionic acids.

REFERENCES:
Darzens, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 152, 1314-1317 and 1601-1603, (1911).
Frankland et al., J. Chem. Soc. 105, 1101-1115, (1914).
Weygand, Preparative Organic Chemistry, pp. 222-223, (1972).
Fieser et al., Reagents for Organic Synthesis, vol. 1, pp. 1160-1161, (1967).

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