US4980505A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Organic synthesis
Assignee: P&G Hair Care Holding Inc
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Filing: 1988-12-16
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Granted: 1990-12-25
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Expires: 2008-12-16
Abstract
Abstract The conversion of ortho-hydroxylated Mannich bases to the corresponding methylated compounds, e.g., cresols, can be effectively carried out using a novel hydrogenation technique.
Inventors
- 👤 Yuh-Guo Pan
- 👤 Lana L. Hochman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 23:33
CPC Classifications
C; C07; C07D; C07D317/00; C07D317/08; C07D317/44; C07D317/46; C07D317/48; C07D317/62; C07D317/64; C07C; C07C213/00; C07C213/08; C07C37/00; C07C37/001; C07C37/002; C07C37/50
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
49 words
A process for the synthesis of ortho-methylated hydroxyaromatic compounds consisting essentially of the steps of hydrogenolysis of an ortho-hydroxylated aromatic Mannich base using about 30 to about 60 psi of hydrogen pressure, in the presence of an aqueous alkaline solvent, and acid precipitation of the result ortho-methylated hydroxyaromatic compound.
Claim 2
Dependent Claim
49 words
A process for the synthesis of ortho-methylated hydroxyaromatic compounds consisting essentially of the steps of hydrogenolysis of an ortho-hydroxylated aromatic Mannich base using about 30 to about 60 psi of hydrogen pressure, in the presence of an aqueous alkaline solvent, and acid precipitation of the result ortho-methylated hydroxyaromatic compound.
Claim 3
Dependent Claim
82 words
The process of claim 1 wherein the Mannich base employed is at least one compound of formula I: ##STR16## wherein X, Y, Z, R 1 , and R 2 can each independently be: hydrogen, alkyl, nitro, amino, alkoxy, halogen, halcalkyl, nitroalkyl, aminoalkyl, aryl, acetamido, haloaryl, alkylaryl, alkoxyaryl; Y and Z may be members of a 5- or 6-membered carbocyclic or heterocyclic ring; R 1 and R 2 may be members, along with N, in a 5- or 6-membered nonaromatic or heterocyclic ring.
Claim 4
Dependent Claim
31 words
The process of claim 2 wherein the Mannich base is of formula II, III, IV or V: ##STR17## wherein X, R 1 and R 2 are as defined in claim 2.
Claim 5
Dependent Claim
11 words
The process of claim 3 wherein the Mannich base is 5-acetamido-2-[(N,N-dimethylamino)methyl]phenol.
Claim 6
Dependent Claim
11 words
The process of claim 4 wherein there is a catalyst present.
Claim 7
Dependent Claim
12 words
The process of claim 5 wherein the catalyst is a palladium/carbon catalyst.
Claim 8
Dependent Claim
12 words
The process of claim 6 wherein the solvent is aqueous potassium hydroxide.
Claim 9
Dependent Claim
15 words
The process of claim 2 wherein a temperature of 70° to 80° C. is employed.
Claim 10
Dependent Claim
15 words
The process of claim 7 wherein a temperature of 70° to 80° C. is employed.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-12-24 | 1994-06-25 | 1994-12-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-12-24 | 1998-06-25 | 1998-12-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-12-24 | 2002-06-25 | 2002-12-25 | $7700.00 | Window Closed / Lapsed |