SU552021A3 - Способ получени производных бифенила или их солей - Google Patents

Способ получени производных бифенила или их солей

Info

Publication number: SU552021A3
Authority: SU; USSR - Soviet Union
Prior art keywords: biphenylyl; salts; acid; fluoro; biphenyl
Prior art date: 1972-08-17

Application number

SU2069774A

Other languages

English (en)

Inventor

Энгель Вольфхард

Тойфель Хельмут

Зеегер Эрнст

Никкль Иозеф

Энгельгардт Гюнтер

Original Assignee

Д-Р Карл Томэ Гмбх (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.)

1972-08-17

Filing date

1974-10-21

Publication date

1977-03-25

1974-10-21 Application filed by Д-Р Карл Томэ Гмбх (Фирма) filed Critical Д-Р Карл Томэ Гмбх (Фирма)

1977-03-25 Application granted granted Critical

1977-03-25 Publication of SU552021A3 publication Critical patent/SU552021A3/ru

Links

150000003839 salts Chemical class 0.000 title description 6
238000000034 method Methods 0.000 title description 3
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
-1 for example Chemical class 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
235000002639 sodium chloride Nutrition 0.000 description 6
239000002904 solvent Substances 0.000 description 6
150000007513 acids Chemical class 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OJSDQQAMDHDTKU-UHFFFAOYSA-N 3-(1-fluoro-4-phenylcyclohexa-2,4-dien-1-yl)butanoic acid Chemical compound FC1(CC=C(C=C1)C1=CC=CC=C1)C(CC(=O)O)C OJSDQQAMDHDTKU-UHFFFAOYSA-N 0.000 description 1
ALIQGQKAABNEKG-UHFFFAOYSA-N 3-(3-fluoro-4-phenylphenyl)but-2-enoic acid Chemical compound FC1=CC(C(=CC(O)=O)C)=CC=C1C1=CC=CC=C1 ALIQGQKAABNEKG-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical group OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
FGIJCCMTPRPJLS-UHFFFAOYSA-N ethyl 3-(3-fluoro-4-phenylphenyl)but-2-enoate Chemical compound FC1=CC(C(C)=CC(=O)OCC)=CC=C1C1=CC=CC=C1 FGIJCCMTPRPJLS-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910052751 metal Chemical class 0.000 description 1
239000002184 metal Chemical class 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical class [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
229910000343 potassium bisulfate Chemical class 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
150000003752 zinc compounds Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
- C07C245/14—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom having diazo groups bound to acyclic carbon atoms of a carbon skeleton
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
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- C07C45/46—Friedel-Crafts reactions
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- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
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Description

Если указанным способом получают еюедине1ше 1)бшей формулы 1, где В означает алкоксигруппу, то они при необходимости могут быть переведены в кислоты (В-оксирадккал) или их соли обшей формулы I.

Если по указанному способу получают кислоту общей формулы 1,то ее затем можно перевести в ее эфиры.

Кислоты обикй формулы 1 могут быть переведены в соли, например в соли с неорганическими или органическими основани ми. В качестве органических оснований особенно пригодными оказа;шсь диэтаноламин, морфолин, циклогексиламин и пиперазин.

Исходные соединени общей формулы II, где А означает группу

сн,

tlH,

i

-(1 СН- vnu -C-CHjполучают , например, путем разложени кетона о(ицей формулы

цинковым соединением соответствующего эфира галоген-уксусной кислоты с получе1шем соеданени общей формулы II, где А означает группу

СНз

- С-СНг ОН

с последующим отщеплением воды от полученного соединени . Получение соединени общей формулы II,где А означает указанную группу, проводит в органическом растворителе, например в простом эфире, таком как диэтиловый эфир, ди меток си эта и, диэтоксиэтан, диоксан, тетрагидрофуран или в смес х этих растворителей, а также в инертном растворителе, таком как бензол или толуол, П 15-120° С, предпочтительно 20-60° С.

Отщепление воды провод т в присутствии водротщепл ющего средства, предпочтительно в присутствии инертного, не смешивающего с водой растворител , примен - водоотщепл юшее средство при нагревании до точки кипени примен емого растворител . В качестве водоотщепл ющего федства могут быть применены кислореагирующие ооли, такие как соли пиридина или алкнлткиридины с галогенводородными кислотами или гидросульфат кали , а также металлические соли, такие как хлорид цинка, далее кислоты, такие как паратолуолсульфонова , фосфорна , серна или, если В означает алкоксигруппу, предпочтительно неорганические галогениды кислоты, как оксигалоге1шды

фосфора. В качестве инертных растворителей примен ют, например, бензол, толуол или ксилол; реакцию можно проводить без растворител .

П р и м е р 1. 3- (2-Ф.тор-4-бифенилил) -масл на кислота.

28,4 г (0,1 мол ) этилового эфира 3- (2 -фто1 4- бифенилил)-2- бутеновой кислоты (т.пл. 52-53°С) раствор ют в 220 мл этанола и, добавл 1 г окиси платины в качестве катализатора,

гидрируют при комнатной температуре и под давлением 5 ата до поглощени рассчитанного количества водорода. Затем отсасьшают катализатор и отгон ют растворитель. Получают 22 г (77% от теоретического этилового эфира 3-(2-фтор-4- бифенллил -масл ной кислотой с т. кип. 154°С/0,1 мм рт. ст.; т.пл. 32-34° С. .

При омылении эфира раствором едкого кали в спирте получают 3- (2 - фтор 4 - бифенилил) масл ную кислоту с т.пл, 98-99° С, Соль мсчэфоли 1а

т.пл. 119- 121°С.

Таким же образом получают следующие соединени : ,

3-(4-фтор-4- бифенилил)-масл ную кислоту с т. гш. 14Ы43°С (этанол);

3-(2-хлор-4-бифенилил) -масл ную кислоту с

т.пл. 128-129° С.

П р и м е р 2. Этиловый эфир 3-(2-фтор-4-бифенилил ) - масл ной кислоты.

65 г (0,299 мол ) этилового эфира 3-(2-фтор

-4-бифенилил)- 2-бутеновой кислоты (т. пл. 52-53°С) раствор ют в 700 мл этанола и, добавл 10 г никел Рене в качестве катализатора, гидрируют при комнатной температуре и под давлением 5 ата до поглощени рассчитанного количества

водорода. Затем отсасывают катализатор и отгон ют растворитель. Получают 52,5 г (79% от теоретического этилового эфира 3- (2фтор-4-бифенилил )-масл ной кислоты с т. кип. 154° С/0,1 мм рт. ст.; т.пл. 32-34°С.

Таким же образом получают из этилового эфира

3-(4 -фтор-4- бифенилил)-2- бутеновой кислоты (т. пл. 60-62° С) с выходом 86% этиловый эфир 3- (4-фтор-4- бифенилил) масл ной кислоты с т. пл. 42-43°С (из петролейного эфира). Свободна

кислота плавитс при 141-143°СГ(из этанола).

П р и м е р 3. 3-(2-Фтор-4- бифенилил)-масл на кислота.

Смесь из 2,56 г (0,01 мол ) 3- (2-фтор-4-бифенилил )- 2-бутеновой кислоты (т. пл. 177-178°С),

2,9 г (0,12 вес.ч.) магниевых стружек и 100мл метанола, перемешива , нагревают приблизительно до 30° С, причем при интенсивном образовании водорода температура повышаетс до 40° С. При этой температуре смесь перемешивают до полного

растворени магни , затем подают в 400 мл лед ной воды и подкисл ют разбавленной сол ной кислотой , экстрагируют с 200 мл эфира, промывают эфирный раствор водой, сушат над сульфатом натри и отгон ют растворитель. Оставшийс

твердый остаток перекристаллизоиьшают из

SU2069774A 1972-08-17 1974-10-21 Способ получени производных бифенила или их солей SU552021A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2240441A DE2240441A1 (de)	1972-08-17	1972-08-17	Neue biphenylderivate und verfahren zur herstellung

Publications (1)

Publication Number	Publication Date
SU552021A3 true SU552021A3 (ru)	1977-03-25

Family

ID=5853790

Family Applications (11)

Application Number	Title	Priority Date	Filing Date
SU1958291A SU482039A3 (ru)	1972-08-17	1973-08-15	Способ получени бифенилилбутеновых кислот или их производных
SU1958288A SU484679A3 (ru)	1972-08-17	1973-08-15	Способ получени производных бифенила
SU1958290A SU511846A3 (ru)	1972-08-17	1973-08-15	Способ получени -бифенилмасл ных кислот или их солей
SU2069110A SU554810A3 (ru)	1972-08-17	1974-10-21	Способ получени производных бифенила или их солей, или рацематов, или оптически активных антиподов
SU2069774A SU552021A3 (ru)	1972-08-17	1974-10-21	Способ получени производных бифенила или их солей
SU2069771A SU520030A3 (ru)	1972-08-17	1974-10-21	Способ получени замещенной бифенилмасл ной кислоты или ее эфира или ее соли
SU2069576A SU561505A3 (ru)	1972-08-17	1974-10-21	Способ получени 3-(4-бифенилил) -масл ной кислоты или ее солей
SU2069114A SU538658A3 (ru)	1972-08-17	1974-10-21	Способ получени бифенилмасл ных кислот или их солей, или рацематов, или оптически активных антиподов
SU2069577A SU520907A3 (ru)	1972-08-17	1974-10-21	Способ получени замещенной бифенилилмасл ной кислоты или ее соли
SU2069578A SU511847A3 (ru)	1972-08-17	1974-10-21	Способ получени замещенной бифенилмасл ной кислоты или ее эфиров или солей
SU7402069575A SU577967A3 (ru)	1972-08-17	1974-10-21	Способ получени замещенной бифенилилмасл ной кислоты или ее эфиров или ее амидов или ее солей

Family Applications Before (4)

Application Number	Title	Priority Date	Filing Date
SU1958291A SU482039A3 (ru)	1972-08-17	1973-08-15	Способ получени бифенилилбутеновых кислот или их производных
SU1958288A SU484679A3 (ru)	1972-08-17	1973-08-15	Способ получени производных бифенила
SU1958290A SU511846A3 (ru)	1972-08-17	1973-08-15	Способ получени -бифенилмасл ных кислот или их солей
SU2069110A SU554810A3 (ru)	1972-08-17	1974-10-21	Способ получени производных бифенила или их солей, или рацематов, или оптически активных антиподов

Family Applications After (6)

Application Number	Title	Priority Date	Filing Date
SU2069771A SU520030A3 (ru)	1972-08-17	1974-10-21	Способ получени замещенной бифенилмасл ной кислоты или ее эфира или ее соли
SU2069576A SU561505A3 (ru)	1972-08-17	1974-10-21	Способ получени 3-(4-бифенилил) -масл ной кислоты или ее солей
SU2069114A SU538658A3 (ru)	1972-08-17	1974-10-21	Способ получени бифенилмасл ных кислот или их солей, или рацематов, или оптически активных антиподов
SU2069577A SU520907A3 (ru)	1972-08-17	1974-10-21	Способ получени замещенной бифенилилмасл ной кислоты или ее соли
SU2069578A SU511847A3 (ru)	1972-08-17	1974-10-21	Способ получени замещенной бифенилмасл ной кислоты или ее эфиров или солей
SU7402069575A SU577967A3 (ru)	1972-08-17	1974-10-21	Способ получени замещенной бифенилилмасл ной кислоты или ее эфиров или ее амидов или ее солей

Country Status (19)

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JP (2)	JPS49124051A (ru)
AT (3)	AT323144B (ru)
AU (2)	AU476340B2 (ru)
BE (3)	BE803734A (ru)
BG (3)	BG21197A3 (ru)
CH (1)	CH588435A5 (ru)
CS (3)	CS165386B2 (ru)
DD (2)	DD107901A5 (ru)
DE (1)	DE2240441A1 (ru)
ES (4)	ES417884A1 (ru)
FR (2)	FR2196167B1 (ru)
GB (2)	GB1410852A (ru)
HU (2)	HU166516B (ru)
IL (2)	IL43003A0 (ru)
NL (2)	NL7311300A (ru)
PL (2)	PL94510B1 (ru)
RO (2)	RO62918A (ru)
SU (11)	SU482039A3 (ru)
ZA (3)	ZA735616B (ru)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2457275A1 (fr) *	1979-05-21	1980-12-19	Fabre Sa Pierre	Acides p-biphenyl-4 methyl-2 buten-3 oiques utiles dans le traitement des rhumatismes
RU2686489C1 (ru) *	2018-12-27	2019-04-29	Федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургский государственный университет (СПбГУ)"	Способ получения α-диазокарбонильных соединений в водной среде

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2162038A1 (de) *	1970-05-05	1972-08-17	William H Rorer Ine , Fort Washington, Pa (V St A )	Verfahren zur Herstellung von synthe tischen Alkansauren und deren Derivaten
BE776316R (fr) *	1971-03-10	1972-06-06	Rorer Inc William H	Nouveaux derives d'acides phenyl-acetiques substitues et procede pour leur

1972
- 1972-08-17 DE DE2240441A patent/DE2240441A1/de active Pending
1973
- 1973-08-14 ES ES417884A patent/ES417884A1/es not_active Expired
- 1973-08-14 AT AT710873A patent/AT323144B/de not_active IP Right Cessation
- 1973-08-14 AT AT711273A patent/AT328427B/de not_active IP Right Cessation
- 1973-08-14 AT AT710773A patent/AT323143B/de not_active IP Right Cessation
- 1973-08-14 CH CH1170773A patent/CH588435A5/xx not_active IP Right Cessation
- 1973-08-14 ES ES417883A patent/ES417883A1/es not_active Expired
- 1973-08-15 DD DD172907A patent/DD107901A5/xx unknown
- 1973-08-15 HU HUTO925A patent/HU166516B/hu unknown
- 1973-08-15 SU SU1958291A patent/SU482039A3/ru active
- 1973-08-15 HU HUTO926A patent/HU166517B/hu unknown
- 1973-08-15 SU SU1958288A patent/SU484679A3/ru active
- 1973-08-15 DD DD172906A patent/DD108071A5/xx unknown
- 1973-08-15 BG BG024327A patent/BG21197A3/xx unknown
- 1973-08-15 BG BG24328A patent/BG22069A3/xx unknown
- 1973-08-15 SU SU1958290A patent/SU511846A3/ru active
- 1973-08-15 BG BG027671A patent/BG21844A3/xx unknown
- 1973-08-16 IL IL43003A patent/IL43003A0/xx unknown
- 1973-08-16 NL NL7311300A patent/NL7311300A/xx unknown
- 1973-08-16 PL PL1973186474A patent/PL94510B1/pl unknown
- 1973-08-16 ZA ZA00735616A patent/ZA735616B/xx unknown
- 1973-08-16 ZA ZA00735628A patent/ZA735628B/xx unknown
- 1973-08-16 GB GB3884473A patent/GB1410852A/en not_active Expired
- 1973-08-16 NL NL7311301A patent/NL7311301A/xx unknown
- 1973-08-16 ZA ZA00735629A patent/ZA735629B/xx unknown
- 1973-08-16 IL IL43004A patent/IL43004A0/xx unknown
- 1973-08-16 JP JP48092052A patent/JPS49124051A/ja active Pending
- 1973-08-16 PL PL1973164708A patent/PL90397B1/pl unknown
- 1973-08-16 CS CS4903A patent/CS165386B2/cs unknown
- 1973-08-16 CS CS4904A patent/CS165387B2/cs unknown
- 1973-08-16 CS CS5793A patent/CS165385B2/cs unknown
- 1973-08-16 JP JP48092053A patent/JPS49124052A/ja active Pending
- 1973-08-16 GB GB3884373A patent/GB1411495A/en not_active Expired
- 1973-08-16 AU AU59309/73A patent/AU476340B2/en not_active Expired
- 1973-08-16 AU AU59308/73A patent/AU5930873A/en not_active Expired
- 1973-08-17 RO RO7300075822A patent/RO62918A/ro unknown
- 1973-08-17 FR FR7330075A patent/FR2196167B1/fr not_active Expired
- 1973-08-17 FR FR7330076A patent/FR2196168B1/fr not_active Expired
- 1973-08-17 BE BE134691A patent/BE803734A/xx unknown
- 1973-08-17 RO RO7300075821A patent/RO62917A/ro unknown
- 1973-08-17 BE BE134689A patent/BE803732A/xx unknown
- 1973-08-17 BE BE134690A patent/BE803733A/xx unknown
1974
- 1974-10-21 SU SU2069110A patent/SU554810A3/ru active
- 1974-10-21 SU SU2069774A patent/SU552021A3/ru active
- 1974-10-21 SU SU2069771A patent/SU520030A3/ru active
- 1974-10-21 SU SU2069576A patent/SU561505A3/ru active
- 1974-10-21 SU SU2069114A patent/SU538658A3/ru active
- 1974-10-21 SU SU2069577A patent/SU520907A3/ru active
- 1974-10-21 SU SU2069578A patent/SU511847A3/ru active
- 1974-10-21 SU SU7402069575A patent/SU577967A3/ru active
- 1974-11-30 ES ES432464A patent/ES432464A1/es not_active Expired
- 1974-11-30 ES ES432465A patent/ES432465A1/es not_active Expired

Also Published As

Publication number	Publication date
RO62917A (fr)	1978-02-15
FR2196167B1 (ru)	1977-04-15
SU511846A3 (ru)	1976-04-25
CS165386B2 (ru)	1975-12-22
AT323144B (de)	1975-06-25
DD108071A5 (ru)	1974-09-05
DD107901A5 (ru)	1974-08-20
IL43003A0 (en)	1973-11-28
AT323143B (de)	1975-06-25
CS165387B2 (ru)	1975-12-22
NL7311300A (ru)	1974-02-19
FR2196168B1 (ru)	1977-02-25
SU577967A3 (ru)	1977-10-25
SU511847A3 (ru)	1976-04-25
ZA735629B (en)	1976-01-28
ZA735616B (en)	1976-01-28
JPS49124052A (ru)	1974-11-27
HU166516B (ru)	1975-03-28
ES417884A1 (es)	1976-03-16
GB1410852A (en)	1975-10-22
SU538658A3 (ru)	1976-12-05
FR2196167A1 (ru)	1974-03-15
SU520907A3 (ru)	1976-07-05
SU554810A3 (ru)	1977-04-15
SU484679A3 (ru)	1975-09-15
CS165385B2 (ru)	1975-12-22
SU561505A3 (ru)	1977-06-05
BG22069A3 (ru)	1976-11-25
PL90397B1 (ru)	1977-01-31
DE2240441A1 (de)	1974-02-28
BE803732A (fr)	1974-02-18
PL94510B1 (pl)	1977-08-31
NL7311301A (ru)	1974-02-19
JPS49124051A (ru)	1974-11-27
AU5930873A (en)	1975-02-20
BG21844A3 (bg)	1976-09-20
HU166517B (ru)	1975-03-28
SU482039A3 (ru)	1975-08-25
ZA735628B (en)	1975-04-30
ES432464A1 (es)	1977-02-16
BE803733A (fr)	1974-02-18
BG21197A3 (bg)	1976-03-20
AU5930973A (en)	1975-02-20
SU520030A3 (ru)	1976-06-30
GB1411495A (en)	1975-10-29
ES417883A1 (es)	1976-11-16
FR2196168A1 (ru)	1974-03-15
IL43004A0 (en)	1973-11-28
CH588435A5 (ru)	1977-05-31
AT328427B (de)	1976-03-25
RO62918A (fr)	1978-04-15
BE803734A (fr)	1974-02-18
ATA711273A (de)	1975-06-15
AU476340B2 (en)	1976-09-16
ES432465A1 (es)	1976-11-16

Publication	Publication Date	Title
Corey	1952	The Mechanism of the Decarboxylation of α, β-and β, γ-Unsaturated Malonic Acid Derivatives and the Course of Decarboxylative Condensation Reactions in Pyridine1
US2359096A (en)	1944-09-26	beta-substituted-delta alpha, beta-gamma-butyrolactones and beta-substituted - beta - hydroxy-gamma-butyrolactones and methods of preparing them
US3077496A (en)	1963-02-12	Process for the preparation of chrysanthemumic acid
SU578883A3 (ru)	1977-10-30	Способ получени пиразолоизохинолинов или их солей
SU453823A3 (ru)	1974-12-15	Способ получения 4-
Russell et al.	1947	The Malonic Ester Synthesis with Styrene Oxide and with Butadiene Oxide1
Drake et al.	1948	The Mercuration of 5-Nitroguaiacol1, 2
US3441605A (en)	1969-04-29	Diketo-dicarboxylic acids and salts and preparation thereof by alkaline oxidation
DE1768856A1 (de)	1971-11-04	Tricyclische Verbindungen
US2582253A (en)	1952-01-15	Synthetic estrogens
US2732379A (en)	1956-01-24
Horning et al.	1951	Glyoxylate Cyclizations. Methoxyindenes1
Niemann et al.	1946	The Reduction of Ethyl a-Benzylamino-β-methoxy-n-caproate with Sodium and Butyl Alcohol
US4713485A (en)	1987-12-15	Process for preparing α-hydroxy-alkanoic acids and compounds obtained by this process
IE43363B1 (en)	1981-02-11	Cyclopropane derivatives
NO742160L (ru)	1975-01-13
Lauer et al.	1939	The Rearrangement of Phenyl Allyl Ethers. VI. The Isomeric Ethyl p-(α-and γ-Ethylallyloxy)-benzoates
US3852333A (en)	1974-12-03	New anthranilic acid{60 -monoglycerides
US2441702A (en)	1948-05-18	1-alkoxy-4-hydroxy-2, 3-dicarbalkoxy naphthalenes
US4010190A (en)	1977-03-01	Precursors for insecticides
DE1793144A1 (de)	1972-02-03	Phenylsalicylsaeure-Verbindungen und Verfahren zu deren Herstellung
US2590086A (en)	1952-03-25	1-hydroxy naphthyl alkanoic acids and certain salts thereof
US2415884A (en)	1947-02-18	Hydroxy-carboxy naphthalenes
Michael et al.	1936	The formation of enolates from lactonic esters
SU520907A3 (ru)	1976-07-05	Способ получени замещенной бифенилилмасл ной кислоты или ее соли