US4010170A
Expired / Lapsed
US
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Butenolide synthesis via carbonylation of vinylmercurials
Assignee: Iowa State University Research Foundation Inc
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Filing: 1975-09-24
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Granted: 1977-03-01
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Expires: 1995-09-24
Abstract
Abstract Compounds containing the butenolide ring have a wide variety of chemical uses. The invention is a method of synthesizing beta -halobutenolides which are valuable intermediates in preparing a variety of butenolide ring containing compounds. The method comprises reacting an acetylenic alcohol with a mercuric halide to provide a vinylmercuric halide and carbonylating the vinylmercuric halide to provide a beta -halobutenolide.
Inventors
- 👤 Richard Craig Larock
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 18:15
CPC Classifications
C; C07; C07D; C07D315/00; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/58
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
80 words
A method of preparing B-halobutenolide, and gamma substituted derivatives thereof, said method comprising, reacting a compound of the formula: ##STR10##wherein R and R' are organic moieties selected to represent the gamma substituents of the particular butenolide being prepared with a mercuric halide to provide a vinylmercuric halide, and carbonylating said vinylmercuric halide, in the presence of a carbonylating agent selected from the group consisting of noble metals and noble metal salts to provide B-halobutenolide or a gamma substituted derivative thereof.
Claim 2
Independent Claim
80 words
A method of preparing B-halobutenolide, and gamma substituted derivatives thereof, said method comprising, reacting a compound of the formula: ##STR10##wherein R and R' are organic moieties selected to represent the gamma substituents of the particular butenolide being prepared with a mercuric halide to provide a vinylmercuric halide, and carbonylating said vinylmercuric halide, in the presence of a carbonylating agent selected from the group consisting of noble metals and noble metal salts to provide B-halobutenolide or a gamma substituted derivative thereof.
Claim 3
Dependent Claim
26 words
The method of claim 1 wherein R and R' are selected from the group consisting of alkyl, aryl, substituted alkyl, substituted aryls, aralkyls, and substituted aralkyls.
Claim 4
Dependent Claim
12 words
The method of claim 1 wherein said mercuric halide is mercuric chloride.
Claim 5
Dependent Claim
21 words
The method of claim 3 wherein said mercuric halide is reacted with said compound of the formula: ##STR11##in an aqueous solvent.
Claim 6
Dependent Claim
13 words
The method of claim 4 wherein said aqueous solvent includes dissolved sodium chloride.
Claim 7
Dependent Claim
17 words
The method of claim 5 wherein said carbonylating occurs in the presence of a noble metal catalyst.
Claim 8
Dependent Claim
24 words
The method of claim 6 wherein said carbonylating occurs in the presence of a polar organic solvent which is inert to the reaction ingredients.
Claim 9
Dependent Claim
27 words
The reaction of claim 7 wherein said vinylmercuric chloride is cooled to temperatures below 0° C., and carbonylation occurs by flushing said vinylmercuric chloride with carbon monoxide.
Claim 10
Independent Claim
49 words
A method of preparing B-halobutenolides, said method comprising, reacting propargyl alcohol with a mercuric halide to provide a vinylmercuric halide, and carbonylating said vinylmercuric halide, in the presence of a carbonylating agent selected from the group consisting of a noble metal and noble metal salts, to provide a B-halobutenolide.
Claim 11
Independent Claim
49 words
A method of preparing B-halobutenolides, said method comprising, reacting propargyl alcohol with a mercuric halide to provide a vinylmercuric halide, and carbonylating said vinylmercuric halide, in the presence of a carbonylating agent selected from the group consisting of a noble metal and noble metal salts, to provide a B-halobutenolide.
Claim 12
Independent Claim
45 words
A method of preparing B-chlorobutenolide, said method comprising, reacting propargyl alcohol with mercuric chloride to provide vinylmercuric chloride, and carbonylating said vinylmercuric chloride, in the presence of a carbonylating agent selected from the group consisting of noble metals and noble metal salts, to provide B-chlorobutenolide.
Claim 13
Independent Claim
45 words
A method of preparing B-chlorobutenolide, said method comprising, reacting propargyl alcohol with mercuric chloride to provide vinylmercuric chloride, and carbonylating said vinylmercuric chloride, in the presence of a carbonylating agent selected from the group consisting of noble metals and noble metal salts, to provide B-chlorobutenolide.
Claim 14
Independent Claim
45 words
A method of preparing B-halobutenolides from trans-2halo-3-hydroxy-1-propenyl-mercuric halide, or substituted derivatives thereof, said method comprising, carbonylating said trans-2-halo-3-hydroxy-1-propenyl-mercuric halide, or a substituted derivative thereof, in the presence of carbonylating agent selected from the group consisting of noble metals and noble metal salts, to provide B-halobutenolides.
Claim 15
Independent Claim
45 words
A method of preparing B-halobutenolides from trans-2halo-3-hydroxy-1-propenyl-mercuric halide, or substituted derivatives thereof, said method comprising, carbonylating said trans-2-halo-3-hydroxy-1-propenyl-mercuric halide, or a substituted derivative thereof, in the presence of carbonylating agent selected from the group consisting of noble metals and noble metal salts, to provide B-halobutenolides.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-02-29 | 1980-08-30 | 1981-03-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-02-29 | 1984-08-30 | 1985-03-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-02-29 | 1988-08-30 | 1989-03-01 | $7700.00 | Window Closed / Lapsed |