Organosilylalkylaromatic compounds
AssigneeConsortium fur Elektrochemische Industrie GmbH
InventorsNorman Haberle, Wolfgang Haas, Leonhard Brader, Franz-Heinrich Kreuzer
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Abstract
The present invention relates to compounds of the formula ##STR1## in which Y represents an organosilicon radical; R" represents a divalent radical which connects the radical Y to the benzene ring via a chain of at least three atoms; X represents a radical of the formula --COOH, --CN, --CHO, --NH.sub.2 or --OH, in which it is possible to block the hydroxyl group with a protecting group; Z represents the same or different substituents in the 2-, 3-, 5- or 6-position to the radical X, preferably hydrogen or halogen atoms; and p represents a value of 0 to 4; and the use of these and related compounds in the preparation of compounds having liquid-crystalline properties.
Claims25
A compound capable of being converted to a liquid crystal having the formula ##STR16## in which n is an integer having a value of at least 2;
- m is an integer having a value of 1, where the sum of n+m is at least 3;
- X is a radical selected from the group consisting of the formula --COOH, --CN, --CHO, and --OH, in which the hydroxyl group may be blocked by a protecting group;
- Y is an organosilicon radical;
- Z is a substituent in the 2-, 3-, 5- or 6-position to the radical X, and p has a value of from 0 to 4.
A process for the preparation of a compound of the formula ##STR21## in which A is selected from the group consisting of Q, and a hydroxyl group which is blocked by a protecting group;
- Q is a halogen atom;
- Z is a substituent in the 2-, 3-, 5- or 6-position to the radical A;
- Y is an organosilicon compound;
- n is an integer having a value of at least 2 and
- p has a value of from 0 to 4;
- which comprises (A) reacting a compound of the formula (VII) ##STR22## in which A, Q, Z and p are the same as above, with magnesium to give a Grignard compound of the formula (VIII) ##STR23## (B) reacting the Grignard compound of formula (VIII) with a compound of formula (IX)
- H.sub.2 C.dbd.CH--(CH.sub.2).sub.n-2 --Q (IX)
- to form a compound of formula (X) ##STR24## (C) reacting a compound of formula (X) with a compound of the formula Y--H in the presence of a catalyst selected from the group consisting of platinum metals and compounds thereof to form a compound of the formula (XI) ##STR25## in which A, Q, Z, Y, n and p are the same as above, and when A in formula (XI) is Q, the compound of formula (XI) is reacted with magnesium and thereafter with CO.sub.2 to convert radical A to a radical the formula --COOH.
A process for preparing a compound of the formula ##STR26## which comprises:
- (A) reacting a compound of the formula (XVI) ##STR27## with a compound of formula (XVII)
- Y--(CH.sub.2).sub.x --E (XVII)
- in which one of the radicals E or G is a radical of the formula --Mg--Q and the other radical is in each case a radical selected from the group consisting of Q and a hydroxyl radical which is blocked by a protecting group;
- x is an integer of from 0 to n-1, with the proviso that if E represents --Mg--Q and the radical --(CH.sub.2).sub.x --E in the formula (XVII) is bonded directly to a silicon atom, x has a value of at least 1;
- A is selected from the group consisting of Q, a hydroxyl group and a carboxyl group which is blocked by a protecting group;
- Y is an organosilicon compound;
- Z is a substituent in the 2-, 3-, 5-, or 6-position to the radical A;
- m is an integer having a value of 0 or 1;
- n is an integer having a value of at least 2, where the sum of n+m is at least 3;
- p has a value of from 0 to 4;
- and
- (B) when A in the compound of formula (VI) is a radical Q, then the resultant compound is reacted with magnesium and thereafter with CO.sub.2 to convert radical A to a radical of the formula --COOH.
A compound of the formula ##STR28## in which M is selected from the group consisting of a halogen atom, a cyano radical, --COCl, --COOH, --CHO, --NH.sub.2 and --OH, where the --OH group may be blocked with a protecting group;
- Y is an organosilicon radical;
- Z is a substituent in the 2-, 3-, 5-, or 6-position to the radical M;
- R" is a divalent radical which connects the radical Y to the benzene ring via a chain of at least three atoms;
- p has a value of from 0 to 4.
A compound of the formula ##STR29## in which Y is an organosilicon radical, R" is a radical of the formula --(O).sub.q --R"".sub.r (--O).sub.s --, where R"" is a divalent hydrocarbon radical having up to 20 carbon atoms or a substituted divalent hydrocarbon radical having up to 20 carbon atoms, q and s each represent a number of 0 or 1, r has a value of 1 to 3 and q, r, s and R"" are selected so that R" is a divalent radical which connects Y to the benzene ring via a chain of at least three atoms;
- X is a radical selected from the group consisting of the formula --COOH, --CN, --CHO and --OH, in which the hydroxyl group may be blocked by a protecting group;
- Z is a substituent in the 2-, 3-, 5- or 6-position to the radical X;
- and p has a value of from 0 to 4.
Dependencies are inferred from the claim text.