Claims
- 1. A method for preparing a derivative of a dibenzoylresorcinol compound, comprising the following steps:
- (a) reacting a mixture of a 4,6-dibenzoylresorcinol and a para-aldehyde with a secondary amine catalyst and a carboxylic acid solvent under reactive conditions to form a methylene carboxylate intermediate in which the methylene bridge forms a linkage between the dibenzoylresorcinol residue and a carboxylate moiety; and then
- (b) reacting the methylene carboxylate compound formed in step (a) with an alcohol or a carboxylic acid in a reactive medium to form the derivative.
- 2. The method of claim 1, wherein the para-aldehyde is paraformaldehyde, and the secondary amine catalyst is selected from the group consisting of diethylamine, dipropyl amine, dibutylamine, dihexylamine, and dioctylamine.
- 3. The method of claim 1, wherein the amount of secondary amine catalyst present is less than about 20 mole %, based on the molar weight of the 4,6-dibenzoylresorcinol.
- 4. The method of claim 3, wherein the amount of secondary amine catalyst present is less than about 10 mole %.
- 5. The method of claim 1, wherein the alcohol employed in step (b) is selected from the group consisting of linear alcohols, branched alcohols, carbocyclic alcohols, heterocyclic alcohols, diols, derivatives of diols, polyols, and functional derivatives of any of the foregoing.
- 6. The method of claim 1, wherein the carboxylic acid employed in step (b) is selected from the group consisting of monocarboxylic acids, polycarboxylic acids, branched derivatives of mono- or polycarboxylic acids; cyclic derivatives of mono- or polycarboxylic acids, and functional derivatives of mono- or polycarboxylic acids.
- 7. A method for preparing a derivative of a dibenzoylresorcinol compound, comprising the following steps:
- (a) reacting a mixture of a 4,6-dibenzoylresorcinol and paraformaldehyde with diethylamine catalyst and acetic acid solvent under reactive conditions to form a methylene carboxylate intermediate in which the methylene bridge forms a linkage between the dibenzoylresorcinol residue and an acetate moiety; and then
- (b) reacting the methylene acetate compound formed in step (a) with an alcohol in a reactive medium to form the derivative, the alcohol being selected from the group consisting of ethanol, isopropanol, tertiary-butanol, 2- hydroxyethylmethacrylate, 1,6-hexanediol, and 2,2,6,6-tetramethyl-4-piperidinol.
- 8. A method for preparing a derivative of a dibenzoylresorcinol compound, comprising the following steps:
- (a) reacting a mixture of a 4,6-dibenzoylresorcinol and paraformaldehyde with diethylamine catalyst and acetic acid solvent under reactive conditions to form a methylene carboxylate intermediate in which the methylene bridge forms a linkage between the dibenzoylresorcinol residue and an acetate moiety; and then
- (b) reacting the methylene acetate compound formed in step (a) with a carboxylic acid in a reactive medium to form the derivative, the carboxylic acid being selected from the group consisting of acrylic acid, methacrylic acid, 2-[2-(methoxyethoxy)ethoxy]acetic acid, and suberic acid.
Parent Case Info
This application is a division of application Ser. No. 08/786,358, filed Jan. 16, 1997, now U.S. Pat. No. 5,981,073, which is hereby incorporated by reference in its entirety.
This application is related to U.S. application Ser. No. 08/669,899 filed Jun. 21, 1996 now U.S. Pat. No. 5,869,185 and U.S. application Ser. No. 08/762,644 filed Dec. 9, 1996 now U.S. Pat. No. 5,763,674.
US Referenced Citations (4)
Number |
Name |
Date |
Kind |
2794052 |
Gordon et al. |
May 1957 |
|
2861976 |
Gordon et al. |
Nov 1958 |
|
3395184 |
Dressler et al. |
Jul 1968 |
|
5391795 |
Pickett |
Feb 1995 |
|
Foreign Referenced Citations (4)
Number |
Date |
Country |
0672732 |
Sep 1995 |
EPX |
0812880 |
Dec 1997 |
EPX |
846673 |
Jun 1998 |
EPX |
1150178 |
Jan 1958 |
FRX |
Non-Patent Literature Citations (2)
Entry |
Abstract: "Benzene Derivatives"--Substituted diacylresorcinols. D.A. Gordon (to Dow Chem. Co., Apr. 19, 1960. p. 14190. |
Abstract: "Noncondensed Aromatics"--20116z--Methylenebis (benzophenone) derivatives. Minagawa, Motonobu, Kubota, Naohiro, Shibata, Toshihiro (Adeka Argus Chem. Col., Ltd) Japan, vol. 91, 1979. |
Divisions (1)
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Number |
Date |
Country |
Parent |
786358 |
Jan 1997 |
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