SU576911A3 - Способ получени эфиров замещенных циклопропанкарбоновой или фенилуксусной кислот - Google Patents

Способ получени эфиров замещенных циклопропанкарбоновой или фенилуксусной кислот

Info

Publication number: SU576911A3
Authority: SU; USSR - Soviet Union
Prior art keywords: methyl; sodium; acid; mixture; dimethyl
Prior art date: 1973-08-23

Application number

SU7402055576A

Other languages

English (en)

Russian (ru)

Inventor

Мизутани Тосио

Оно Нобуо

Уме Еситака

Мацуо Такаси

Original Assignee

Сумитомо Кемикал Компани Лимитед (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.)

1973-08-23

Filing date

1974-08-05

Publication date

1977-10-15

1973-08-23 Priority claimed from JP9498073A external-priority patent/JPS5212697B2/ja

1973-08-28 Priority claimed from JP48097063A external-priority patent/JPS5228790B2/ja

1974-08-05 Application filed by Сумитомо Кемикал Компани Лимитед (Фирма) filed Critical Сумитомо Кемикал Компани Лимитед (Фирма)

1977-10-15 Application granted granted Critical

1977-10-15 Publication of SU576911A3 publication Critical patent/SU576911A3/ru

Links

238000000034 method Methods 0.000 title description 10
239000002253 acid Substances 0.000 title description 9
150000002148 esters Chemical class 0.000 title description 7
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title description 6
150000007513 acids Chemical class 0.000 title description 3
-1 methyl -1 - propenyl Chemical group 0.000 description 34
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
239000011734 sodium Substances 0.000 description 9
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 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
238000003756 stirring Methods 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
150000002431 hydrogen Chemical class 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000010410 layer Substances 0.000 description 4
XLOPRKKSAJMMEW-SFYZADRCSA-N (+)-trans-chrysanthemic acid Chemical compound CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
230000003993 interaction Effects 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
XLOPRKKSAJMMEW-SFYZADRCSA-M (R,R)-chrysanthemate Chemical compound CC(C)=C[C@@H]1[C@@H](C([O-])=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-M 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
229960002903 benzyl benzoate Drugs 0.000 description 2
230000015572 biosynthetic process Effects 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
238000006243 chemical reaction Methods 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
LDFPTHJERYPPKM-UHFFFAOYSA-M triethyl-[(3-phenoxyphenyl)methyl]azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC(OC=2C=CC=CC=2)=C1 LDFPTHJERYPPKM-UHFFFAOYSA-M 0.000 description 2
239000008096 xylene Substances 0.000 description 2
XNICSRPFAIGZAB-UHFFFAOYSA-M 1-[(3-phenoxyphenyl)methyl]pyridin-1-ium;chloride Chemical compound [Cl-].C=1C=CC=C[N+]=1CC(C=1)=CC=CC=1OC1=CC=CC=C1 XNICSRPFAIGZAB-UHFFFAOYSA-M 0.000 description 1
UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 description 1
125000006017 1-propenyl group Chemical group 0.000 description 1
SFHVXKNMCGSLAR-UHFFFAOYSA-N 2,2,3,3-tetramethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C(O)=O)C1(C)C SFHVXKNMCGSLAR-UHFFFAOYSA-N 0.000 description 1
IPCVATIPXJBOCH-UHFFFAOYSA-N 2-(2-methylpent-4-en-2-yl)propanedioic acid Chemical compound CC(C(C(=O)O)C(=O)O)(CC=C)C IPCVATIPXJBOCH-UHFFFAOYSA-N 0.000 description 1
IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 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
101150075558 CHGA gene Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
QXKAIJAYHKCRRA-JJYYJPOSSA-N D-arabinonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(O)=O QXKAIJAYHKCRRA-JJYYJPOSSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
241000124033 Salix Species 0.000 description 1
101100018999 Streptomyces cattleya pcbC gene Proteins 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000005210 alkyl ammonium group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
150000003938 benzyl alcohols Chemical class 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
BUBWTSJXUHKBBX-UHFFFAOYSA-N ethyl acetate;sodium Chemical compound [Na].CCOC(C)=O BUBWTSJXUHKBBX-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000006289 hydroxybenzyl group Chemical group 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
HQIZDGAMCWYBKS-UHFFFAOYSA-M sodium;cyclopropanecarboxylate Chemical compound [Na+].[O-]C(=O)C1CC1 HQIZDGAMCWYBKS-UHFFFAOYSA-M 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
UIOXYHBIXWFNKN-UHFFFAOYSA-M triethyl-[(3-phenoxyphenyl)methyl]azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC(OC=2C=CC=CC=2)=C1 UIOXYHBIXWFNKN-UHFFFAOYSA-M 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

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

SU7402055576A 1973-08-23 1974-08-05 Способ получени эфиров замещенных циклопропанкарбоновой или фенилуксусной кислот SU576911A3 (ru)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP9498073A JPS5212697B2 (cs)	1973-08-23	1973-08-23
JP48097063A JPS5228790B2 (cs)	1973-08-28	1973-08-28

Publications (1)

Publication Number	Publication Date
SU576911A3 true SU576911A3 (ru)	1977-10-15

Family

ID=26436207

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU7402055576A SU576911A3 (ru)	1973-08-23	1974-08-05	Способ получени эфиров замещенных циклопропанкарбоновой или фенилуксусной кислот

Country Status (2)

Country	Link
CS (1)	CS183755B2 (cs)
SU (1)	SU576911A3 (cs)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN113387800A (zh) *	2021-06-09	2021-09-14	浙江理工大学	一种3,5-二甲氧基苯甲酸甲酯的制备方法

1974
- 1974-08-05 CS CS554174A patent/CS183755B2/cs unknown
- 1974-08-05 SU SU7402055576A patent/SU576911A3/ru active

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN113387800A (zh) *	2021-06-09	2021-09-14	浙江理工大学	一种3,5-二甲氧基苯甲酸甲酯的制备方法

Also Published As

Publication number	Publication date
CS183755B2 (en)	1978-07-31

Publication	Publication Date	Title
JPH0355442B2 (cs)	1991-08-23
DE1468553C2 (cs)	1971-09-30
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US4485257A (en)	1984-11-27	Process for preparing racemized cyclopropanecarboxylic acids or their derivatives
US20100029979A1 (en)	2010-02-04	Process for preparing (meth)acrylic acid
CH615411A5 (cs)	1980-01-31
US4000181A (en)	1976-12-28	α-Cyano-phenoxybenzyl cyclopropane carboxylate insecticides
CN102040480A (zh)	2011-05-04	一种3,3,3-三氟丙醇的合成方法
US4128572A (en)	1978-12-05	Process for preparing phenylacetic acid
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JPS5912093B2 (ja)	1984-03-21	シクロブタノンまたはシクロブテノンの製法
US3969393A (en)	1976-07-13	Process for preparing cyclopropane-carboxylic acid esters
CA1155456A (en)	1983-10-18	Intermediates in the preparation of cyclopropanecarboxylate esters and process for their manufacture
CN105601517B (zh)	2017-12-22	一种3,3,3‑三氟丙酸甲酯的合成方法
US4351961A (en)	1982-09-28	2-(2',2'-Dichloro-3',3',3'-trifluoropropyl)- and 2-(2',2',3'-trichloro-3',3'-difluoropropyl)-4-chlorocyclobutan-1-ones
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Islam et al.	1996	Cyclopent-2-en-1-ones from [3+ 2]-annulation of 3-ethoxycarbonyl-2-propenylidene (triphenyl)-phosphorane and glyoxals: Synthesis of cis-jasmone
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DE10232167A1 (de)	2003-01-30	Verfahren zur Racemisierung einer optisch aktiven vinylsubstituierten Cyclopropancarbonsäureverbindung
GB700391A (en)	1953-12-02	Improvements in or relating to basic esters and processes for preparing the same
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JP2595683B2 (ja)	1997-04-02	ラセミー菊酸無水物のトランス化方法
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SU576911A3 - Способ получени эфиров замещенных циклопропанкарбоновой или фенилуксусной кислот - Google Patents

Info

Links

Landscapes

Applications Claiming Priority (2)

Publications (1)

Family

ID=26436207

Family Applications (1)

Country Status (2)

Cited By (1)

Cited By (1)

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