SU608468A3 - Способ получени 2-хлорциклобутанонов или 2-хлорциклобутен2-онов - Google Patents

Способ получени 2-хлорциклобутанонов или 2-хлорциклобутен2-онов

Info

Publication number: SU608468A3
Authority: SU; USSR - Soviet Union
Prior art keywords: compound; mmol; acid; mixture; added
Prior art date: 1974-09-04

Application number

SU752170510A

Other languages

English (en)

Russian (ru)

Inventor

Якобус Ван Ден Бринк Маринус (Нидерланды)

Антониус Крамер Петрус (Нидерланды)

Аустермюле-Бертола Хелена (Швейцария)

Original Assignee

Шелл Интернэшнл Рисерч Маатсхаппий Б.В., (Фирма)

Priority date (The priority date 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 date listed.)

1974-09-04

Filing date

1975-09-02

Publication date

1978-05-25

1975-09-02 Application filed by Шелл Интернэшнл Рисерч Маатсхаппий Б.В., (Фирма) filed Critical Шелл Интернэшнл Рисерч Маатсхаппий Б.В., (Фирма)

1978-05-25 Application granted granted Critical

1978-05-25 Publication of SU608468A3 publication Critical patent/SU608468A3/ru

Links

238000000034 method Methods 0.000 title claims description 5
STJYMUBZVMSMBP-UHFFFAOYSA-N chlorocyclobutane Chemical class ClC1CCC1 STJYMUBZVMSMBP-UHFFFAOYSA-N 0.000 title 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 15
239000011701 zinc Substances 0.000 claims description 11
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 10
229910052725 zinc Inorganic materials 0.000 claims description 10
235000019270 ammonium chloride Nutrition 0.000 claims description 5
-1 benzyloxymethyl Chemical group 0.000 claims description 4
229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 4
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
230000020477 pH reduction Effects 0.000 claims description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
229940120124 dichloroacetate Drugs 0.000 claims 1
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
150000001875 compounds Chemical class 0.000 description 24
239000000203 mixture Substances 0.000 description 22
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 18
239000000243 solution Substances 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical compound CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000010410 layer Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
238000009835 boiling Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 2
239000008235 industrial water Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
PQQUGMKIQAFPOI-UHFFFAOYSA-N 2-chloro-3,3-dimethyl-4-(propan-2-yloxymethyl)cyclobutan-1-one Chemical compound CC(C)OCC1C(=O)C(Cl)C1(C)C PQQUGMKIQAFPOI-UHFFFAOYSA-N 0.000 description 1
DICHVGMVHVJMHO-UHFFFAOYSA-N 2-chlorocyclobut-2-en-1-one Chemical class ClC1=CCC1=O DICHVGMVHVJMHO-UHFFFAOYSA-N 0.000 description 1
125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
UATRONWBYDQKSQ-UHFFFAOYSA-N 3-methyl-1-(3-methylbut-2-enoxy)but-2-ene Chemical compound CC(C)=CCOCC=C(C)C UATRONWBYDQKSQ-UHFFFAOYSA-N 0.000 description 1
GQUXMDLPOJYAQR-UHFFFAOYSA-N 4-chloro-2,2,3,3-tetramethylcyclobutan-1-one Chemical compound CC1(C)C(Cl)C(=O)C1(C)C GQUXMDLPOJYAQR-UHFFFAOYSA-N 0.000 description 1
BBEJKLYWJWHPDE-UHFFFAOYSA-N 4-chloro-3-ethyl-2,2-dimethylcyclobutan-1-one Chemical compound CCC1C(Cl)C(=O)C1(C)C BBEJKLYWJWHPDE-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
101000909811 Homo sapiens Protein cornichon homolog 2 Proteins 0.000 description 1
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 1
102100024446 Protein cornichon homolog 2 Human genes 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
GMGLYSIINJPYLI-UHFFFAOYSA-N butan-2-one;propan-2-one Chemical compound CC(C)=O.CCC(C)=O GMGLYSIINJPYLI-UHFFFAOYSA-N 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
239000002826 coolant Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical class O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 description 1
238000010908 decantation Methods 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000003993 interaction Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/517—Saturated compounds containing a keto group being part of a ring containing ether groups, groups, groups, or groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SU752170510A 1974-09-04 1975-09-02 Способ получени 2-хлорциклобутанонов или 2-хлорциклобутен2-онов SU608468A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB3864474A GB1524682A (en)	1974-09-04	1974-09-04	Process for the preparation of cyclobutanones

Publications (1)

Publication Number	Publication Date
SU608468A3 true SU608468A3 (ru)	1978-05-25

Family

ID=10404792

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU752170510A SU608468A3 (ru)	1974-09-04	1975-09-02	Способ получени 2-хлорциклобутанонов или 2-хлорциклобутен2-онов

Country Status (3)

Country	Link
BE (1)	BE832980A (fr)
GB (1)	GB1524682A (fr)
SU (1)	SU608468A3 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5420356A (en) *	1993-08-11	1995-05-30	Sumitomo Chemical Company, Limited	Process for producing cyclobutanones
EP3766862B1 (fr)	2019-07-17	2023-06-07	Shin-Etsu Chemical Co., Ltd.	Composés de diméthylcyclobutanone, composés de diméthylcyclobutane et leurs procédés de préparation
ES2951876T3 (es)	2019-07-17	2023-10-25	Shinetsu Chemical Co	Compuesto diéster que tiene un anillo de dimetilciclobutano, un procedimiento para preparar el mismo, y un procedimiento para preparar compuesto de dimetilciclobutano derivado del compuesto diéster

1974
- 1974-09-04 GB GB3864474A patent/GB1524682A/en not_active Expired
1975
- 1975-09-02 SU SU752170510A patent/SU608468A3/ru active
- 1975-09-02 BE BE159664A patent/BE832980A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
GB1524682A (en)	1978-09-13
BE832980A (fr)	1976-03-02

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Matsuura et al.	1960	Model Reactions for the Biosynthesis of Thyroxine. III. The Synthesis of Hindered Quinol Ethers and their Conversion to Hindered Analogs of Thyroxine1, 2
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DE1768680A1 (de)	1972-10-19	Verfahren zur Herstellung olefinischer Verbindungen aus Phosphoniumsalzen,Carbonylverbindungen und Epoxiden
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Dey	1937	222. The jaborandi alkaloids. Part I. The synthesis of homo-and iso homo-pilopic acids and of r-pilocarpidine and r-iso pilocarpidine by new methods and the resolution of r-pilocarpine
Rahman et al.	1980	Conjugate addition reactions of some magnesium-based organocuprates with α-ethylenic carbonyl compounds
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