Patent US3868401A successfully refreshed from Google Patents.
US3868401A
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Asymmetric synthesis of alkyl chrysanthemates
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1972-08-01
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Granted: 1975-02-25
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Expires: 1992-08-01
Abstract
Abstract The invention relates to a process for preparing an optically active alkyl chrysanthemate which comprises reacting 2,5dimethyl-2,4-hexadiene with an alkyl diazoacetate in the presence of a copper complex coordinated with (a) chiral ligand(s).
Inventors
- 👤 Tadatoshi Aratani
- 👤 Shuzo Nakamura
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 14:43
CPC Classifications
C; C07; C07C; C07C67/00; C07C67/30; C07C67/333; C07C69/00; C07C69/608; B; B01; B01J; B01J2531/00; B01J2531/10; B01J2531/16; C07B; C07B2200/00; C07B2200/07; C07C2601/00; C07C2601/02
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
34 words
A PROCESS FOR PREPARING AN OPTICALLY ACTIVE ALKYL CHRYSANTHEMATE WHICH COMPRISES REACTING 2,5-DIMETHYL-2,4HEXADIENE WITH AN ALKYL DIAZOACETATE IN THE PRESENCE OF A COPPER CATALYST COORDINATED WITH A CHIRAL LIGAND CAPABLE OF COMPLEXING WITH COPPER.
Claim 2
Dependent Claim
34 words
A PROCESS FOR PREPARING AN OPTICALLY ACTIVE ALKYL CHRYSANTHEMATE WHICH COMPRISES REACTING 2,5-DIMETHYL-2,4HEXADIENE WITH AN ALKYL DIAZOACETATE IN THE PRESENCE OF A COPPER CATALYST COORDINATED WITH A CHIRAL LIGAND CAPABLE OF COMPLEXING WITH COPPER.
Claim 3
Dependent Claim
82 words
The process of claim 1 in which said copper-ligand complex is a compound of divalent copper which is given the formula: Cu(A*)n wherein A* is an anionic conjugate base derived from a chiral compound selected from: a. Beta -dicarbonyl compounds, b. Beta -ketoimines, c. oxyimines, d. amino-alcohols, e. amino acids, or f. carboxylic acids, and wherein n 1 or 2 determined by the number of negative charge of the said anionic conjugate base to neutralize the positive charge of the cupric ion.
Claim 4
Dependent Claim
75 words
The process of claim 1 in which said copper-ligand complex is a compound of univalent copper which is given the formula: (L*)nCuX wherein L* is an electrically neutral chiral ligand selected from: a. phosphines with chiral carbon, b. phosphines with chiral phosphorus, or c. phosphites witH chiral carbon, and n is an integer between 1 and 4, and wherein X is a univalent anion selected from: a. chloride, b. bromide, c. iodide, or d. perchlorate.
Claim 5
Dependent Claim
28 words
The process of claim 2 in which said chiral compound is a Schiff''s base which is prepared by combining a chiral primary amine and a derivative of salicylaldehyde.
Claim 6
Dependent Claim
19 words
The process of claim 4 in which said chiral primary amine is a derivative of Alpha , Beta -diphenylethylamine.
Claim 7
Dependent Claim
36 words
The process of claim 5 in which said derivative of Alpha , Beta -diphenylethylamine is a. Alpha , Beta -diphenylethylamine, b. Alpha -phenyl- Beta -(p-tolyl)ethylamine, c. Alpha -(p-tolyl)- Beta -phenylethylamine, or d. Alpha -phenyl- Beta -(p-chlorophenyl)ethylamine.
Claim 8
Dependent Claim
24 words
The process of claim 4 in which said salicylaldehyde derivative is a. salicylaldehyde, b. o-vanillin, c. 3,5-dibromosalicylaldehyde, d. 2-hydroxy-3-isopropyl-6-methylbenzaldehyde, e. 2-hydroxy-acetophenone, or f. 2-hydroxy-1-naphthaldehyde.
Claim 9
Dependent Claim
20 words
The process of claim 1 in which the alcoholic part of the said alkyl diazoacetate is a lower aliphatic alcohol.
Claim 10
Dependent Claim
17 words
The process of claim 1 in which the reaction is conducted in the absence of a solvent.
Claim 11
Dependent Claim
17 words
The process of claim 1 in which the reaction is conducted in the presence of a solvent.
Claim 12
Dependent Claim
13 words
The process of claim 10 in which said solvent is an alkyl benzene.
Claim 13
Dependent Claim
12 words
The process of claim 11 in which said alkyl benzene is toluene.
Claim 14
Dependent Claim
19 words
The process of claim 1 in which the reaction is conducted at a selected temperature between -50*C. and 150*C.
Claim 15
Dependent Claim
20 words
The process of claim 10 in which the reaction is conducted at a temperature below the freezing temperature of 2,5-dimethyl-2,4-hexadiene.
References Cited (Backward Citations)
GB740014A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-02-24 | 1978-08-26 | 1979-02-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-02-24 | 1982-08-26 | 1983-02-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-02-24 | 1986-08-26 | 1987-02-25 | $7700.00 | Window Closed / Lapsed |