Process for the preparation of optically active aryloxyalkanoic

Details Process for the preparation of optically active aryloxyalkanoic Process for the preparation of optically active aryloxyalkanoic

1985-07-30

1988-08-23

Rotman, Alan L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546301, 560 56, 560 61, 560 62, 562466, 562471, 562472, C07D21364, C07C 6976, C07C 6988

Patent

active

047662204

ABSTRACT:
The invention relates to the preparation of optically active aryloxyalkanoic acid derivatives of the formula ##STR1## in which Ar represents an optionally substituted phenyl, naphthyl, phenoxy or pyridyloxy radical, R represents a C.sub.1 -C.sub.4 -alkyl radical and A represents a --COOR.sub.1, ##STR2## or --CO--Z radical, Z being halogen. It consists in reacting an aqueous or aqueous-organic solution of an optically active alkali metal salt of a 2-halogeno-alkanoic acid with an aqueous solution of an alkali metal salt of the phenol of the formula Ar-OH at an elevated temperature under a pressure less than the vapor pressure of water at the chosen temperature.
It permits the preparation of aryloxyalkanoic acid derivatives with a very high content of the isomer having the D configuration, which can be used as herbicides.

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Gilman, Organic Synthesis, Coll. Vol. I, pp.-75-76, (John Wiley & Sons, New York, 1941).
Gilman, Organic Chemistry, vol. I, pp. 264-271, (John Wiley & Sons, New York, 1943).
Remick, Electronic Interpretations of Organic Chemistry, pp. 381-382, (John Wiley & Sons, New York, 1949).
Lowry, Mechanisms and Theory in Organic Chemistry, Harper and Row, New York, 1976, pp.-174-179).
March, Advanced Organic Chemistry, Reaction, Mechanisms and Structure, McGraw-Hill Pub., pp. 90-95, (1968).

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