Method of manufacturing an aminoaryl-containing organosilicon compound and method of manufacturing an intermediate product of the aforementioned compound
View Patent ↗To provide an aminoaryl-containing organosilicon compound with high efficiency, after protecting amino groups of a haloaniline compound with a specific compound, to form a Grignard reagent and to deprotect the aforementioned groups by reacting the Grignard reagent with a silicon compound.
1. A method of manufacturing an aminoaryl-containing organosilicon compound represented by general formula (6):
(where R 6 , R 7 , R 8 , R 9 , R 10 , Y, n, and m are the same as defined below) by subjecting an organosilicon compound of general formula (1):
where
R 1 , R 2 , R 3 , and R 4 independently represent alkyl groups with 1 to 4 carbon atoms;
R 5 represents an alkylene group with 1 to 6 carbon atoms;
R 6 , R 7 , R 8 , and R 9 independently represent a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, or an alkoxy group with 1 to 4 carbon atoms;
R 10 represents a univalent hydrocarbon group;
Y represents a hydrolysable group;
n is an integer from 1 to 4; and
m is an integer from 1 to n,
to a deprotection reaction.
2. A method as set forth in claim 1 wherein R 5 represents an ethylene group.
3. A method as set forth in claim 1 wherein m is 1 and n is greater than 1.
4. A method as set forth in claim 1 wherein m is equal to n.
5. A method as set forth in claim 1 wherein the deprotection reaction is carried out between a compound having an active hydrogen atom and the organosilicon compound of general formula (1).
6. A method as set forth in claim 5 wherein the deprotection reaction is carried out in the presence of a catalyst.
7. A method as set forth in claim 6 wherein the catalyst is an acidic compound.
8. A method as set forth in claim 7 wherein the acidic compound is further defined as a mineral acid or its salt.
9. A method as set forth in claim 8 wherein the acidic compound is selected from the group of hydrochloric acid, sulfuric acid, or ammonium chloride.
10. A method as set forth in claim 6 wherein the catalyst is a basic compound.
11. A method as set forth in claim 10 wherein the basic compound is further defined as a metal hydroxide or alkoxide.
12. A method as set forth in claim 11 wherein the basic compound is selected from the group of sodium hydroxide, potassium hydroxide, or sodium methoxide.
13. A method as set forth in claim 5 wherein the compound having the active hydrogen comprises a hydroxyl group.
14. A method as set forth in claim 1 wherein deprotection is carried out without the presence of solvent.
15. A method as set forth in claim 1 further comprising the step of purifying the compound of general formula (6).
16. A method as set forth in claim 15 wherein the compound of general formula (6) is purified via stripping.