# US 5,350,873 A · Optically active phenoxypropionic esters

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- Number: US 5,350,873 A
- Document ID: US5350873A
- Status: Granted
- Kind: A
- Application number: 07/928,568
- Filed: 1992-08-13
- Granted: 1994-09-27
- Earliest claimed: 1991-08-16
- Assignees: BASF SE
- Inventors: Volker Bach; Wolfgang Brox; Karl-Heinz Etzbach; Axel Paul; Karl Siemensmeyer
- Web page: https://patentgrep.com/patent/US5350873A

## CPC

- C08G 63/60: derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
- C07C 69/712: the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
- C07C 69/92: with etherified hydroxyl groups
- C07C 69/94: of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
- C08F 20/30: containing aromatic rings in the alcohol moiety
- C09K 19/586: {Optically active dopants; chiral dopants}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

Optically active compounds of the formula I ##STR1## where R is C.sub.1 -C.sub.12 -alkyl or -perfluoroalkyl in which one or two non-adjacent CH.sub.2 or CF.sub.2 groups can also be replaced by --O-- and/or --CO-- and/or --CO--O-- and/or --CH.dbd.CH-- and/or --CH-halogen-- and/or --CHCN-- and/or --0--CO--CH-halogen-- and/or --O--CO--CHCN--, or is C.sub.1 -C.sub.12 -alkyl which can have a terminal chemically reactive group and in which a CH.sub.2 group can be replaced by --O--, A.sup.1 and A.sup.2 are each, independently of one another, 1,4-phenylene which is unsubstituted or substituted by one or two F and/or Cl and/or Br atoms and/or CH.sub.3 groups and/or CN groups and in which one or two CH groups can also be replaced by N, 1,4-cyclohexylene in which one or two non-adjacent CH.sub.2 groups can also be replaced by --O-- and/or --S--, 1,4-piperidinediyl, 1,4-bicyclo[2.2.2]octylene, 2,6-naphthalenediyl, decahydro-2,6-naphthalenediyl or 1,2,3,4-tetrahydro-2,6-naphthalenediyl, A.sup.3 is unsubstituted or substituted phenyl, Z is --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --C.tbd.C-- or a single bond and m is 0, 1, 2 or 3.

## Claims

### Claim 1

An optically active compound of the formula I
where
R is C.sub.1 -C.sub.12 -alkyl or -perfluoroalkyl in which each of one or two non-adjacent CH.sub.2 or CF.sub.2 groups can be replaced by --O--, --CO--, --CO--O--, --CH.dbd.CH--, --CH-halogen--, --O--CO--CHCN--, or is C.sub.1 -C.sub.12 -alkyl which can have a terminal chemically reactive group selected from the group consisting of CH.sub.2 .dbd.CH--, HO--, ##STR33## where R.sup.2 is H, CH.sub.3 or C.sub.2 H.sub.5,
R.sup.3 is --OH or --Cl, and
R.sup.4 is H, Cl or CH.sub.3.
and in which a CH.sub.2 group can be replaced by --O--,
A.sup.1 and A.sup.2 are each, independently of the other:
1. 4-phenylene which is unsubstituted or substituted by one or two members of the group consisting of F, Cl, Br, CH.sub.3 and CN groups and in which one or two CH groups of the phenylene ring can be replaced by N;
1,4-cyclohexylene in which one or two non-adjacent CH.sub.2 groups can be replaced by --O-- or --S--;
1,4-piperidinediyl;
1,4-bicyclo[2.2.2]octylene;
2,6-naphthalenediyl;
decahydro-2,6-naphthalenediyl; or
1,2,3,4-tetrahydro-2,6-naphthalenediyl,
A.sup.3 is unsubstituted or substituted phenyl,
Z is --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, OCH.sub.2 --, --CH.sub.2 O, --C.dbd.C--, or a single bond, and
m is 1, 2, or 3,
with the proviso that when m is 2 or 3, the radicals A.sup.1 and Z in the individual --(A.sup.1 --Z) groups can be identical or different.

### Claim 2

An optically active compound of the formula I ##STR34## where R is C.sub.1 -C.sub.12 -alkyl or -perfluoroalkyl in which each of one or two non-adjacent CH.sub.2 or CF.sub.2 groups can be replaced by --O--, --CO--, --CO--O--, --CH.dbd.CH--, --CH-halogen--, --O--CO--CHCN--, or is C.sub.1 -C.sub.12 -alkyl which can have a terminal chemically reactive group selected from the group consisting of CH.sub.2 .dbd.CH--, HO--, ##STR35## where R.sup.2 is H, CH.sub.3 or C.sub.2 H.sub.5,
R.sup.3 is --OH or --Cl, and
R.sup.4 is H, Cl or CH.sub.3,
and in which a CH.sub.2 group can be replaced by --O--,
A.sup.1 and A.sup.2 are each, independently of the other:
1. 4-phenylene which is unsubstituted or substituted by one or two members of the group consisting of F, Cl, Br, CH.sub.3 and CN groups and in which one or two CH groups of the phenylene ring can be replaced by N;
1,4-cyclohexylene in which one or two non-adjacent CH.sub.2 groups can be replaced by --O-- or --S--;
1,4-piperidinediyl;
1. 4-bicyclo[2.2.2]octylene;
2,6-naphthalenediyl;
decahydro-2,6-naphthalenediyl; or
1,2,3,4-tetrahydro-2,6-naphthalenediyl,
A.sup.3 is phenyl substituted by one or two members which are independently selected from the group consisting of C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.10 -alkoxy, F, Cl, and Br,
Z is --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, OCH.sub.2 --, --CH.sub.2 O, --C.dbd.C--, or a single bond, and
m is 0, 1, 2, or 3,
with the proviso that when m is 2 or 3, the radicals A.sup.1 and Z in the individual --(A.sup.1 --Z) groups can be identical or different.

### Claim 3 (depends on 1)

An optically active compound as defined in claim 1, wherein m is 1 or 2.

### Claim 4 (depends on 1)

An optically active compound as defined in claim 1, wherein m is 2.

### Claim 5 (depends on 1)

An optically active compound as defined in claim 1, wherein Z is --CO--O--, --O--CO-- or a single bond.

### Claim 6 (depends on 1)

An optically active compound as defined in claim 1, wherein R is C.sub.5 -C.sub.11 -alkyl or C.sub.5 -C.sub.11 -alkoxy.

### Claim 7 (depends on 1)

An optically active compound as defined in claim 1, wherein A.sup.1 and A.sup.2 are each 1,4-phenylene.

### Claim 8 (depends on 1)

An optically active compound as defined in claim 1, wherein A.sup.3 is phenyl.

### Claim 9 (depends on 1)

An optically active compound as defined in claim 1, wherein A.sup.3 is phenyl which has one or two C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.10 -alkoxy, bromine or chlorine substituents which are independent of one another.

### Claim 10 (depends on 2)

An optically active compound of claim 2, wherein m is 1.

### Claim 11 (depends on 2)

An optically active compound of claim 2, wherein m is 2.

### Claim 12 (depends on 2)

An optically active compound of claim 2, wherein Z is --CO--O--, --O--CO--, or a single bond.

### Claim 13 (depends on 2)

An optically active compound of claim 2, wherein R is C.sub.5 -C.sub.11 -alkyl or C.sub.5 -C.sub.11 -alkoxy.

### Claim 14 (depends on 2)

An optically active compound of claim 2, wherein A.sup.1 and A.sup.2 are each 1,4-phenylene.

### Claim 15 (depends on 2)

An optically active compound of claim 2, wherein A.sup.3 is phenyl.

### Claim 16 (depends on 2)

An optically active compound of claim 2, wherein A.sup.3 is phenyl which has one or two C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.10 -alkoxy, Br, or Cl substituents which are independent of one another.

### Claim 17

An optically active compound having the formula ##STR36##