US 11,866,443 B2
Method for separating optically active hydroxy cineole derivatives
Klaus Ditrich, Ludwigshafen (DE); Michael Rack, Ludwigshafen (DE); Stefan Benson, Ludwigshafen (DE); Roland Goetz, Ludwigshafen (DE); and Helmut Kraus, Research Triangle Park, NC (US)
Assigned to BASF AGRO B.V., Arnhem (NL)
Appl. No. 16/614,400
Filed by BASF Agro B.V., Arnhem (NL)
PCT Filed May 9, 2018, PCT No. PCT/EP2018/062042
§ 371(c)(1), (2) Date Nov. 18, 2019,
PCT Pub. No. WO2018/210663, PCT Pub. Date Nov. 22, 2018.
Claims priority of application No. 17171875 (EP), filed on May 19, 2017.
Prior Publication US 2020/0148697 A1, May 14, 2020
Int. Cl. C07D 493/08 (2006.01); C07B 57/00 (2006.01)
CPC C07D 493/08 (2013.01) [C07B 57/00 (2013.01); C07B 2200/07 (2013.01)] 8 Claims
 
1. A method for separating an optically active hydroxy cineole derivative of formula (I-R),

OG Complex Work Unit Chemistry
or an optically active hydroxy cineole derivative of formula (I-S),

OG Complex Work Unit Chemistry
wherein
R1 is methyl and
R2 is isopropyl;
from a mixture comprising the enantiomers of formula (I-R) and formula (I-S), the method comprising the steps of:
i) Providing a suspension comprising a mixture of the enantiomers of formula (I-R) and formula (I-S), wherein the desired enantiomer is present in the mixture in an amount of ≥51 to ≤95 wt.-%, related to the sum of the enantiomers of the mixture, in at least one non-polar solvent;
ii) Separating the desired enantiomer by lixiviation consisting of stirring the suspension obtained in step (i) at temperature in the range of ≥10° C. to reflux temperature of the non-polar solvent such that the desired enantiomer is separated from soluble substances, wherein the desired enantiomer is present as an insoluble material; and
iii) Isolating the desired enantiomer obtained in step (ii) by filtration.