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
EP3766861B1 (fr)	2019-07-17	2023-05-24	Shin-Etsu Chemical Co., Ltd.	Composé diester doté d'un anneau diméthylcyclobutane, son procédé de préparation et procédé de préparation d'un composé diméthylcyclobutane dérivé du composé diester

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

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Marvel et al.	1958	Polymeric Phthalocyanines. II1
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Sato et al.	1980	Copper-catalyzed reaction of grignard reagents with. BETA.-propiolactones: A convenient method for the synthesis of. BETA.-substituted propionic acids.
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Toland Jr et al.	1953	Reactions of Toluic Acids with Sulfur. I. Stilbenedicarboxylic Acids
Berson et al.	1958	The Synthesis and Complete Resolution of 2-Hydroxy-1, 1'-binaphthyl and the Reaction of its Phenylglyoxylate with Methylmagnesium Iodide1, 2
Kuzma et al.	1984	Generation of the Dianion of N-(Trimethylsilyl) acetamide and Reaction of the Dianion with Electrophilic Reagents
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
Kaeding et al.	1965	Oxidation of Aromatic Acids. VI. Reaction of Cupric Salts of Carboxylic Acids with Aromatic Aprotic Compounds
AU661884B2 (en)	1995-08-10	Process for making arylacrylic acids
Berens et al.	1995	The First Stereoselective Synthesis of Racemic. beta.-Multistriatin: A Pheromone Component of the European Elm Bark Beetle Scolytus multistriatus (Marsh.)
Wolinsky et al.	1976	Geometrical isomers of. gamma.-bisabolene
Jacobson et al.	1953	Studies in tetrazole chemistry. I. Side chain acid derivatives
DE1768680A1 (de)	1972-10-19	Verfahren zur Herstellung olefinischer Verbindungen aus Phosphoniumsalzen,Carbonylverbindungen und Epoxiden
Birkinshaw	1952	Studies in the biochemistry of micro-organisms. 88. Palitantin. Part 2. Further derivatives and degradation products
Jacobson	1957	Constituents of Heliopsis Species. V. Heliopsin, a Second Insecticidal Amide from the Roots of H. helianthoides var. scabra.
Rahman et al.	1980	Conjugate addition reactions of some magnesium-based organocuprates with α-ethylenic carbonyl compounds