FR2494271A1 - Procede de preparation de chlorolactones a partir d'acides carboxyliques insatures - Google Patents
Procede de preparation de chlorolactones a partir d'acides carboxyliques insatures Download PDFInfo
- Publication number
- FR2494271A1 FR2494271A1 FR8024393A FR8024393A FR2494271A1 FR 2494271 A1 FR2494271 A1 FR 2494271A1 FR 8024393 A FR8024393 A FR 8024393A FR 8024393 A FR8024393 A FR 8024393A FR 2494271 A1 FR2494271 A1 FR 2494271A1
- Authority
- FR
- France
- Prior art keywords
- acid
- chloro
- chlorolactone
- carboxylic acid
- process according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 18
- 150000001735 carboxylic acids Chemical class 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title abstract description 3
- 239000002253 acid Substances 0.000 claims abstract description 27
- -1 CARBOXYL FUNCTION Chemical group 0.000 claims abstract description 11
- WHTNHYRHHHFFBV-UHFFFAOYSA-N ClNS(=O)=O Chemical compound ClNS(=O)=O WHTNHYRHHHFFBV-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 230000000269 nucleophilic effect Effects 0.000 claims abstract description 4
- 150000001721 carbon Chemical class 0.000 claims abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 claims description 3
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- XQOCAGXQSXUMHJ-UHFFFAOYSA-N 5-hydroxyhex-2-enoic acid Chemical compound CC(O)CC=CC(O)=O XQOCAGXQSXUMHJ-UHFFFAOYSA-N 0.000 claims 1
- 101800001194 Crustacean hyperglycemic hormone 2 Proteins 0.000 claims 1
- 241001331845 Equus asinus x caballus Species 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- SKQZZOAYLKPINN-UHFFFAOYSA-N n,4-dichlorobenzenesulfonamide;sodium Chemical compound [Na].ClNS(=O)(=O)C1=CC=C(Cl)C=C1 SKQZZOAYLKPINN-UHFFFAOYSA-N 0.000 claims 1
- SJUGPXBWZCQTKM-UHFFFAOYSA-N n-chloro-4-methylbenzenesulfonamide;sodium Chemical compound [Na].CC1=CC=C(S(=O)(=O)NCl)C=C1 SJUGPXBWZCQTKM-UHFFFAOYSA-N 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 229920001577 copolymer Polymers 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 abstract description 2
- 239000011347 resin Substances 0.000 abstract description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 abstract 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 229940098779 methanesulfonic acid Drugs 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000012264 purified product Substances 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- HPLJEKXDAFHJPD-UHFFFAOYSA-N 5-(chloromethyl)oxolan-2-one Chemical compound ClCC1CCC(=O)O1 HPLJEKXDAFHJPD-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000002635 aromatic organic solvent Substances 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- OOYVIBWKRAKPPC-UHFFFAOYSA-N chlorylformic acid Chemical class OC(=O)Cl(=O)=O OOYVIBWKRAKPPC-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YVWBQGFBSVLPIK-UHFFFAOYSA-N cyclohex-2-ene-1-carboxylic acid Chemical compound OC(=O)C1CCCC=C1 YVWBQGFBSVLPIK-UHFFFAOYSA-N 0.000 description 1
- VUSWCWPCANWBFG-UHFFFAOYSA-N cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC=CC1 VUSWCWPCANWBFG-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000007245 halolactonization reaction Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- SVPRVJIDOLJYQR-UHFFFAOYSA-N n-chlorobenzenesulfonamide;sodium Chemical compound [Na].ClNS(=O)(=O)C1=CC=CC=C1 SVPRVJIDOLJYQR-UHFFFAOYSA-N 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- AIJKNFNVBXPDEJ-UHFFFAOYSA-N phenylmethanesulfonamide;sodium Chemical compound [Na].NS(=O)(=O)CC1=CC=CC=C1 AIJKNFNVBXPDEJ-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Epoxy Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8024393A FR2494271A1 (fr) | 1980-11-14 | 1980-11-14 | Procede de preparation de chlorolactones a partir d'acides carboxyliques insatures |
| DE19813144765 DE3144765A1 (de) | 1980-11-14 | 1981-11-11 | Verfahren zur herstellung von chlorlactonen aus ungesaettigten carbonsaeuren |
| NL8105148A NL8105148A (nl) | 1980-11-14 | 1981-11-13 | Werkwijze ter bereiding van chloorlactonverbindingen uitgaande onverzadigde carbonzuren. |
| US06/321,145 US4413133A (en) | 1980-11-14 | 1981-11-13 | Process for manufacturing chlorolactones from unsaturated carboxylic acids |
| GB8134276A GB2087396B (en) | 1980-11-14 | 1981-11-13 | Production of chlorolactones from unsaturated carboxylic acids and novel chlorolactones so produced |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8024393A FR2494271A1 (fr) | 1980-11-14 | 1980-11-14 | Procede de preparation de chlorolactones a partir d'acides carboxyliques insatures |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2494271A1 true FR2494271A1 (fr) | 1982-05-21 |
| FR2494271B1 FR2494271B1 (show.php) | 1983-12-02 |
Family
ID=9248050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8024393A Granted FR2494271A1 (fr) | 1980-11-14 | 1980-11-14 | Procede de preparation de chlorolactones a partir d'acides carboxyliques insatures |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4413133A (show.php) |
| DE (1) | DE3144765A1 (show.php) |
| FR (1) | FR2494271A1 (show.php) |
| GB (1) | GB2087396B (show.php) |
| NL (1) | NL8105148A (show.php) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4948905A (en) * | 1989-09-18 | 1990-08-14 | Iowa State University Reasearch Foundation, Inc. | Synthesis of vinyl lactones |
| JP3097143B2 (ja) | 1991-02-21 | 2000-10-10 | チッソ株式会社 | 生理活性物質合成用光学活性化合物の製造法および光学活性中間体化合物 |
| WO2017115257A1 (en) * | 2015-12-28 | 2017-07-06 | Sabic Global Technologies B.V. | Methods for producing 1-pentanols, 4-pentenoic acids, 4-pentenols, and 1-pentanoic acids |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3870747A (en) * | 1971-11-24 | 1975-03-11 | Merck & Co Inc | Intermediates and process for prostaglandin synthesis |
| US4010170A (en) * | 1975-09-24 | 1977-03-01 | Iowa State University Research Foundation, Inc. | Butenolide synthesis via carbonylation of vinylmercurials |
| EP0031932B1 (de) * | 1979-12-22 | 1987-07-01 | Hüls Troisdorf Aktiengesellschaft | Substituierte Lactone, Pentacarbonsäurederivate und Verfahren zu ihrer Herstellung |
-
1980
- 1980-11-14 FR FR8024393A patent/FR2494271A1/fr active Granted
-
1981
- 1981-11-11 DE DE19813144765 patent/DE3144765A1/de not_active Withdrawn
- 1981-11-13 GB GB8134276A patent/GB2087396B/en not_active Expired
- 1981-11-13 NL NL8105148A patent/NL8105148A/nl not_active Application Discontinuation
- 1981-11-13 US US06/321,145 patent/US4413133A/en not_active Expired - Fee Related
Non-Patent Citations (2)
| Title |
|---|
| EXBK/54 * |
| EXBK/80 * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2494271B1 (show.php) | 1983-12-02 |
| GB2087396A (en) | 1982-05-26 |
| US4413133A (en) | 1983-11-01 |
| GB2087396B (en) | 1984-08-30 |
| DE3144765A1 (de) | 1982-06-16 |
| NL8105148A (nl) | 1982-06-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |