التفاصيل البيبلوغرافية
| العنوان: |
Polycyclic dihydroxy compound and methods for preparation |
| Document Number: |
20070123713 |
| تاريخ النشر: |
May 31, 2007 |
| Appl. No: |
11/289070 |
| Application Filed: |
November 29, 2005 |
| مستخلص: |
A process of forming a polycyclic dihydroxy compound is described. The polycyclic dihydroxy compound has Formula (I) [chemical expression included] wherein R1, R2 and R3 are independently at each occurrence selected from the group consisting of a cyano functionality, a halogen, an aliphatic functionality having 1 to 10 carbons, a cycloaliphatic functionality having 3 to 10 carbons, and an aromatic functionality having 6 to 10 carbons; and wherein each occurrence of “n”, “m”, and “p” independently has a value of 0, 1, 2, 3, or 4. Also described are polycyclic dihydroxy compounds of Formula (I) in which the phthalimide group is meta to the triaryl-substituted carbon. |
| Inventors: |
Raj, T. Tilak (Bangalore, IN); Radhakrishna, A.S. (Bangalore, IN); Lens, Jan-Pleun (Breda, NL); K., Subrahmanya Bhat (Mangalore, IN); Hasyagar, Umesh (Bangalore, IN) |
| Claim: |
1. A process of forming a polycyclic dihydroxy compound, comprising: reacting a phenol compound of Formula (II) with a nitro-substituted acetophenone compound of Formula (III) in the presence of an aromatic sulfonic acid to produce a nitro-substituted polycyclic dihydroxy compound of Formula (IV) [chemical expression included] wherein R1 and R2 are independently at each occurrence selected from the group consisting of a cyano functionality, a halogen, an aliphatic functionality having 1 to 10 carbons, a cycloaliphatic functionality having 3 to 10 carbons, and an aromatic functionality having 6 to 10 carbons; and wherein each occurrence of “n” and “m” independently has a value of 0, 1, 2, 3, or 4; reducing the nitro-substituted polycyclic dihydroxy compound of Formula (IV) to produce an amine-substituted polycyclic dihydroxy compound of Formula (V) [chemical expression included] reacting the amine-substituted polycyclic dihydroxy compound of Formula (V) with a phthalic anhydride compound of Formula (VI) to produce a phthalimide-substituted polycyclic dihydroxy compound of Formula (I) [chemical expression included] wherein R3 is independently at each occurrence selected from the group consisting of a cyano functionality, a halogen, an aliphatic functionality having 1 to 10 carbons, a cycloaliphatic functionality having 3 to 10 carbons, and an aromatic functionality having 6 to 10 carbons; and wherein each occurrence of “p” independently has a value of 0, 1, 2, 3,or 4. |
| Claim: |
2. The process of claim 1 wherein the phenol compound is phenol. |
| Claim: |
3. The process of claim 1 wherein the nitro-substituted acetophenone compound is 3-nitroacetophenone, 4-nitroacetophenone, or a combination thereof. |
| Claim: |
4. The process of claim 1, wherein the aromatic sulfonic acid is para-toluenesulfonic acid. |
| Claim: |
5. The process of claim 1, wherein the aromatic sulfonic acid is used in an amount of about 0.2 to about 3 moles per mole of the nitro-substituted acetophenone compound. |
| Claim: |
6. The process of claim 1, wherein reacting the phenol compound with the nitro-substituted acetophenone compound occurs at a temperature of about 60° C. to about 160° C. for a time of about 30 hours to about 70 hours. |
| Claim: |
7. The process of claim 1, wherein reducing the nitro-substituted polycyclic dihydroxy compound is accomplished by reacting the nitro-substituted polycyclic dihydroxy compound with hydrogen in the presence of a catalyst comprising palladium on carbon. |
| Claim: |
8. The process of claim 1, wherein reducing the nitro-substituted polycyclic dihydroxy compound occurs at a temperature of about 30° C. to about 80° C. |
| Claim: |
9. The process of claim 1 wherein the phthalic anhydride compound is phthalic anhydride. |
| Claim: |
10. The process of claim 1 wherein the amine-substituted polycyclic dihydroxy compound is reacted with the phthalic anhydride compound in the presence of acetic acid. |
| Claim: |
11. The process of claim 1, wherein the amine-substituted polycyclic dihydroxy compound is reacted with the phthalic anhydride compound at a temperature of about 60° C. to about 110° C. |
| Claim: |
12. A process of forming a polycyclic dihydroxy compound, comprising: reacting phenol with a nitro-substituted acetophenone compound selected from 3-nitroacetophenone, 4-nitroacetophenone, and mixtures thereof, in the presence of p-toluenesulfonic acid to produce a nitro-substituted polycyclic dihydroxy compound of Formula (VII) [chemical expression included] reducing the nitro-substituted polycyclic dihydroxy compound with hydrogen in the presence of a palladium on carbon catalyst to produce an amine-substituted polycyclic dihydroxy compound of Formula (VIII) [chemical expression included] reacting the amine-substituted polycyclic dihydroxy compound with phthalic anhydride in acetic acid to produce a phthalimide-substituted polycyclic dihydroxy compound of Formula (IX) [chemical expression included] |
| Claim: |
13. A polycyclic dihydroxy compound produced by the process of claim 1, wherein the phthalimide group of Formula (IX) is meta to the triaryl-substituted carbon. |
| Claim: |
14. A polycyclic dihydroxy compound produced by the process of claim 12, wherein the nitro-substituted acetophenone compound comprises 3-nitroacetophenone. |
| Claim: |
15. A compound of Formula (X) [chemical expression included] wherein R1, R2 and R3 are independently at each occurrence selected from the group consisting of a cyano functionality, a halogen, an aliphatic functionality having 1 to 10 carbons, a cycloaliphatic functionality having 3 to 10 carbons, and an aromatic functionality having 6 to 10 carbons; and wherein each occurrence of “n”, “m”, and “p” independently has a value of 0, 1, 2, 3, or 4. |
| Claim: |
16. The compound of claim 15, wherein each occurrence of “m”, “n”, and “p” is zero. |
| Current U.S. Class: |
548476/000 |
| Current International Class: |
07 |
| رقم الانضمام: |
edspap.20070123713 |
| قاعدة البيانات: |
USPTO Patent Applications |