US3855301A
Expired / Lapsed
US
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Novel dihydrochalcone and process
Assignee: Procter and Gamble Co
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Filing: 1971-06-28
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Granted: 1974-12-17
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Expires: 1991-06-28
Abstract
Abstract A novel artificial sweetener compound, 3-(mhydroxyphenyl)phloropropiophenone and a process for preparing same, as well as other 3-arylphloropropiophenones, from aryl aldehydes and phloroglucinol.
Inventors
- 👤 G Rizzi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 02:06
CPC Classifications
C; C07; C07C; C07C255/00; A; A23; A23L; A23L27/00; A23L27/30; C07C45/00; C07C49/00; C07C49/76; C07C49/82; C07C49/83
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
1 words
3-(M-HYDRROXYPHENYL)PHLOROPROPIOPHENONE.
Claim 2
Dependent Claim
1 words
3-(M-HYDRROXYPHENYL)PHLOROPROPIOPHENONE.
Claim 3
Dependent Claim
133 words
A process for preparing 3-arylphloropropiophenones comprising: (1) heating an aromatic aldehyde of the formula ArCHO, wherein Ar is selected from the group consisting of 3-hydroxyphenyl and 3-hydroxy-4-alkoxyphenyl, with cyanoacetic acid in the presence of an acid or base catalyst to form an Alpha -cyanocinnamic acid derivative; (2) reducing the Alpha -cyanocinnamic acid derivative prepared in Step (1) to provide the corresponding Alpha -cyano- Beta -arylpropionic acid; (3) decarboxylating the Alpha -cyano- Beta -arylpropionic acid prepared in Step (2) by heating to form the corresponding Beta -aryl-propionitrile; (4) condensing the Beta -arylpropionitrile prepared in Step (3) with phloroglucinol in the presence of a mild Lewis acid to form a phloroglucinol condensate in the immonium salt form; and (5) boiling the immonium salt prEpared in Step (4) in water to provide the desired 3-arylphloropropiophenone compound.
Claim 4
Dependent Claim
133 words
A process for preparing 3-arylphloropropiophenones comprising: (1) heating an aromatic aldehyde of the formula ArCHO, wherein Ar is selected from the group consisting of 3-hydroxyphenyl and 3-hydroxy-4-alkoxyphenyl, with cyanoacetic acid in the presence of an acid or base catalyst to form an Alpha -cyanocinnamic acid derivative; (2) reducing the Alpha -cyanocinnamic acid derivative prepared in Step (1) to provide the corresponding Alpha -cyano- Beta -arylpropionic acid; (3) decarboxylating the Alpha -cyano- Beta -arylpropionic acid prepared in Step (2) by heating to form the corresponding Beta -aryl-propionitrile; (4) condensing the Beta -arylpropionitrile prepared in Step (3) with phloroglucinol in the presence of a mild Lewis acid to form a phloroglucinol condensate in the immonium salt form; and (5) boiling the immonium salt prEpared in Step (4) in water to provide the desired 3-arylphloropropiophenone compound.
Claim 5
Dependent Claim
20 words
A process according to claim 2 wherein the aromatic aldehyde is selected from the group consisting of m-hydroxybenzaldehyde and isovanillin.
Claim 6
Dependent Claim
18 words
A process according to claim 2 wherein Step (1) is carried out using ammonium acetate as the catalyst.
References Cited (Backward Citations)
US3087821A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1977-12-16 | 1978-06-17 | 1978-12-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1981-12-16 | 1982-06-17 | 1982-12-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1985-12-16 | 1986-06-17 | 1986-12-17 | $7700.00 | Window Closed / Lapsed |