CA1081251A - Preparation de 3-alkyl-cyclopentane-1, 2-diones et de leurs intermediaires - Google Patents

Preparation de 3-alkyl-cyclopentane-1, 2-diones et de leurs intermediaires

Info

Publication number: CA1081251A
Authority: CA; Canada
Prior art keywords: cyclopentane; alkyl; dicarboalkoxy; dione; ene
Prior art date: 1973-12-19
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.): Expired

Application number

CA323,372A

Other languages

English (en)

Inventor

Thurman C. Mcfearin (Jr.)

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

El Paso Products Co

Original Assignee

El Paso Products Co

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.)

1973-12-19

Filing date

1979-03-09

Publication date

1980-07-08

1973-12-19 Priority claimed from US426021A external-priority patent/US3922296A/en

1979-03-09 Application filed by El Paso Products Co filed Critical El Paso Products Co

1979-03-09 Priority to CA323,372A priority Critical patent/CA1081251A/fr

1980-07-08 Application granted granted Critical

1980-07-08 Publication of CA1081251A publication Critical patent/CA1081251A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 31
238000002360 preparation method Methods 0.000 title claims abstract description 16
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 13
229910052751 metal Inorganic materials 0.000 claims abstract description 11
239000002184 metal Substances 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
230000002152 alkylating effect Effects 0.000 claims abstract description 9
150000001350 alkyl halides Chemical class 0.000 claims abstract description 8
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 24
-1 alkali metal alkoxide Chemical class 0.000 claims description 18
150000002148 esters Chemical class 0.000 claims description 15
229910052783 alkali metal Inorganic materials 0.000 claims description 13
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 8
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 8
235000006408 oxalic acid Nutrition 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 7
238000009833 condensation Methods 0.000 claims description 7
230000005494 condensation Effects 0.000 claims description 7
239000003880 polar aprotic solvent Substances 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 3
239000000543 intermediate Substances 0.000 abstract description 4
241000208140 Acer Species 0.000 abstract description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
238000006243 chemical reaction Methods 0.000 description 19
OACYKCIZDVVNJL-UHFFFAOYSA-N 3-Methyl-1,2-cyclopentanedione Chemical compound CC1CCC(=O)C1=O OACYKCIZDVVNJL-UHFFFAOYSA-N 0.000 description 18
238000005804 alkylation reaction Methods 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
230000029936 alkylation Effects 0.000 description 12
239000000047 product Substances 0.000 description 10
239000001837 2-hydroxy-3-methylcyclopent-2-en-1-one Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000000010 aprotic solvent Substances 0.000 description 8
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 8
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 8
XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000005903 acid hydrolysis reaction Methods 0.000 description 5
239000007859 condensation product Substances 0.000 description 5
239000013078 crystal Substances 0.000 description 5
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 5
239000000203 mixture Substances 0.000 description 5
CFAKWWQIUFSQFU-UHFFFAOYSA-N 2-hydroxy-3-methylcyclopent-2-en-1-one Chemical compound CC1=C(O)C(=O)CC1 CFAKWWQIUFSQFU-UHFFFAOYSA-N 0.000 description 4
YVLNMBVALLUHCX-UHFFFAOYSA-N [Na].[Na].C1(C=CCC1)=O Chemical class [Na].[Na].C1(C=CCC1)=O YVLNMBVALLUHCX-UHFFFAOYSA-N 0.000 description 4
229940093499 ethyl acetate Drugs 0.000 description 4
235000019439 ethyl acetate Nutrition 0.000 description 4
WOPKYMRPOKFYNI-UHFFFAOYSA-N hydroxycyclopentenone Natural products OC1=CCCC1=O WOPKYMRPOKFYNI-UHFFFAOYSA-N 0.000 description 4
229940102396 methyl bromide Drugs 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
238000003756 stirring Methods 0.000 description 4
WMMUOLWPQBGCOJ-UHFFFAOYSA-N 2-hydroxy-3-methylcyclopent-2-en-1-one;3-methylcyclopentane-1,2-dione Chemical compound CC1CCC(=O)C1=O.CC1=C(O)C(=O)CC1 WMMUOLWPQBGCOJ-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 3
229940045348 brown mixture Drugs 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
238000006482 condensation reaction Methods 0.000 description 3
239000000796 flavoring agent Substances 0.000 description 3
235000013355 food flavoring agent Nutrition 0.000 description 3
239000000463 material Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000002002 slurry Substances 0.000 description 3
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000013019 agitation Methods 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
CIISBNCSMVCNIP-UHFFFAOYSA-N cyclopentane-1,2-dione Chemical compound O=C1CCCC1=O CIISBNCSMVCNIP-UHFFFAOYSA-N 0.000 description 2
JAJTUXWGRFAHNS-UHFFFAOYSA-N dimethyl 4,5-dioxocyclopentane-1,3-dicarboxylate;sodium Chemical compound [Na].[Na].COC(=O)C1CC(C(=O)OC)C(=O)C1=O JAJTUXWGRFAHNS-UHFFFAOYSA-N 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
229940113088 dimethylacetamide Drugs 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012467 final product Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
NDDRGLVIZAHCHY-UHFFFAOYSA-N 1-o-ethyl 3-o-methyl 4-methoxy-1-methyl-5-oxocyclopent-3-ene-1,3-dicarboxylate Chemical compound CCOC(=O)C1(C)CC(C(=O)OC)=C(OC)C1=O NDDRGLVIZAHCHY-UHFFFAOYSA-N 0.000 description 1
VFVPLXRMJQPBSH-UHFFFAOYSA-N 2,2-dichlorocyclopentan-1-one Chemical compound ClC1(Cl)CCCC1=O VFVPLXRMJQPBSH-UHFFFAOYSA-N 0.000 description 1
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
GDTHVMAIBQVUMV-UHFFFAOYSA-N 2-oxopentanal Chemical compound CCCC(=O)C=O GDTHVMAIBQVUMV-UHFFFAOYSA-N 0.000 description 1
QEEIYWNOARXWFK-UHFFFAOYSA-N 3-o-ethyl 1-o-methyl 4,5-dioxocyclopentane-1,3-dicarboxylate;sodium Chemical class [Na].[Na].CCOC(=O)C1CC(C(=O)OC)C(=O)C1=O QEEIYWNOARXWFK-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
238000006418 Brown reaction Methods 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
241000758791 Juglandaceae Species 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 1
RYOZIZYOUJTSOR-UHFFFAOYSA-N OC=1C(CCC1CCCC)=O.C(CCC)C1C(C(CC1)=O)=O Chemical compound OC=1C(CCC1CCCC)=O.C(CCC)C1C(C(CC1)=O)=O RYOZIZYOUJTSOR-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
125000005250 alkyl acrylate group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000010923 batch production Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
230000000875 corresponding effect Effects 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
YBNVRZYZOMEGBU-UHFFFAOYSA-N cyclopentane-1,2-dione;sodium Chemical compound [Na].[Na].O=C1CCCC1=O YBNVRZYZOMEGBU-UHFFFAOYSA-N 0.000 description 1
230000000911 decarboxylating effect Effects 0.000 description 1
HVJKFGWSZJBLJB-UHFFFAOYSA-N diethyl 4,5-dioxocyclopentane-1,3-dicarboxylate;sodium Chemical compound [Na].[Na].CCOC(=O)C1CC(C(=O)OCC)C(=O)C1=O HVJKFGWSZJBLJB-UHFFFAOYSA-N 0.000 description 1
CTJCBQSPTUBEAE-UHFFFAOYSA-N diethyl 4-methoxy-1-methyl-5-oxocyclopent-3-ene-1,3-dicarboxylate Chemical compound CCOC(=O)C1=C(OC)C(=O)C(C)(C(=O)OCC)C1 CTJCBQSPTUBEAE-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
SIUPGUKZIKSKCV-UHFFFAOYSA-N dimethyl 4-methoxy-1-methyl-5-oxocyclopent-3-ene-1,3-dicarboxylate Chemical compound COC(=O)C1=C(OC)C(=O)C(C)(C(=O)OC)C1 SIUPGUKZIKSKCV-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000005454 flavour additive Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
229940040102 levulinic acid Drugs 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000003901 oxalic acid esters Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000012071 phase Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000036647 reaction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000002311 subsequent effect Effects 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000011269 tar Substances 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA323,372A 1973-12-19 1979-03-09 Preparation de 3-alkyl-cyclopentane-1, 2-diones et de leurs intermediaires Expired CA1081251A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA323,372A CA1081251A (fr)	1973-12-19	1979-03-09	Preparation de 3-alkyl-cyclopentane-1, 2-diones et de leurs intermediaires

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US426021A US3922296A (en)	1973-12-19	1973-12-19	Novel process for the preparation of cyclopentane-1, 2-diones and intermediates therefor
CA215,579A CA1056848A (fr)	1973-12-19	1974-12-10	Procede pour la preparation de 3-alkylcyclopentane-1,2-diones et de leurs intermediaires
CA323,372A CA1081251A (fr)	1973-12-19	1979-03-09	Preparation de 3-alkyl-cyclopentane-1, 2-diones et de leurs intermediaires

Publications (1)

Publication Number	Publication Date
CA1081251A true CA1081251A (fr)	1980-07-08

Family

ID=27163742

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA323,372A Expired CA1081251A (fr)	1973-12-19	1979-03-09	Preparation de 3-alkyl-cyclopentane-1, 2-diones et de leurs intermediaires

Country Status (1)

Country	Link
CA (1)	CA1081251A (fr)

1979
- 1979-03-09 CA CA323,372A patent/CA1081251A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-07-08	MKEX	Expiry

Publication	Publication Date	Title
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US4977264A (en)	1990-12-11	Process for the production of 4,5-dichloro-6-ethylpyrimidine
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CA1081251A (fr)	1980-07-08	Preparation de 3-alkyl-cyclopentane-1, 2-diones et de leurs intermediaires
CA1056848A (fr)	1979-06-19	Procede pour la preparation de 3-alkylcyclopentane-1,2-diones et de leurs intermediaires
US4168280A (en)	1979-09-18	Method for synthesis of 2-hydroxy-3-methyl cyclopent-2-ene-1-one
US3969466A (en)	1976-07-13	Preparation of hydrazodicarbonamide
US4007216A (en)	1977-02-08	2-Methoxy-4-methyl-3-oxo-cyclopent-1-ene-1,4-dicarboxylic acid esters
US4393008A (en)	1983-07-12	2-Cyano-2-(3-phenoxy-phenyl)-propionic acid amide and preparation thereof
US5177247A (en)	1993-01-05	Process for the preparation of hydroxyphenylpropionates
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US2865962A (en)	1958-12-23	Preparation of 3-methyl-1, 2-cyclopentanedione
US4131747A (en)	1978-12-26	Process for preparing α-substituted phenylalkanecarboxylic acid
SU1116977A3 (ru)	1984-09-30	Способ получени 3,3-диметилаллилового спирта
SU1205756A3 (ru)	1986-01-15	Способ получени 1,1-дихлор-4-метилпентадиенов
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