SU511847A3 - Method for preparing substituted biphenylbutyric acid or its esters or salts - Google Patents

Method for preparing substituted biphenylbutyric acid or its esters or salts

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SU511847A3
SU511847A3 SU2069578A SU2069578A SU511847A3 SU 511847 A3 SU511847 A3 SU 511847A3 SU 2069578 A SU2069578 A SU 2069578A SU 2069578 A SU2069578 A SU 2069578A SU 511847 A3 SU511847 A3 SU 511847A3
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acid
general formula
salts
chj
carried out
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Энгель Вольфхард
Тойфель Хельмут
Зеегер Эрнст
Никкль Иозеф
Энгельгардт Гюнтер
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Д-Р Карл Томэ Гмбх (Фирма)
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Description

Исходные соединени  общей формулы I получают из 2 - (4 - бифенилцл) -1 1 - пропилгалогенида общей формулы IIIThe starting compounds of general formula I are obtained from 2 - (4 - biphenyl) -1 1 - propyl halide of general formula III

НаЕNaE

где Hal означает атом галогена, предпочтительно ,атом йода ил  брома,where Hal means a halogen atom, preferably an iodine atom of bromine,

путем переведени  в соединение Гринь ра с пскледующим взаимодействием с параформальдегидом . Взаимодействие провод т в простом эфире, например в диэтиловом эфире или диоксане, при нагревании до температуры кипени  примен емых растворителей. Соедине1т  общей формулы UJ могут быть получены, например, взаимодействием замещенного соо1ветственно бифенила с хлоридом моноэтилОвого эфира щавелевой кислоты и безводным хлоридом алюмини , причем образуетс  соответствующий эфир 2 - (4 - бифенилил) глиоксиловой кислоты, из которого вместе с 1 мол. магнийметилбромида получают 2 - (4 - бифенилнл) - 2 океипропиоповую кислоту.by transferring to the Grignard compound with the following interaction with paraformaldehyde. The reaction is carried out in a simple ether, for example diethyl ether or dioxane, while heating the boiling point of the solvents used. Compounds of the general formula UJ can be obtained, for example, by reacting a substituted respectively biphenyl with oxalic acid monoethyl ester chloride and anhydrous aluminum chloride, and the corresponding 2- (4-biphenylyl) glyoxylic acid ester is formed, from which 1 mol. magnesium methyl bromide get 2 - (4 - biphenyl) - 2 okeipropiopovoy acid.

Известными методами восстановлени , например с применением йодистоводородной кислоты в уксусной кислоте, можно получить соответствующую 2 - (4 - бифенилил) пропионовую кислоту; восстанавлива  эту кислоту алюмшшйгидридом лити  в простом эфире, синтезируют 2 - (4 - бифенилил ) пропанол обшей формулы IVBy the known methods of reduction, for example using hydroiodic acid in acetic acid, the corresponding 2- (4-biphenylyl) propionic acid can be obtained; By reducing this acid with lithium alumina hydrate in ether, it is synthesized 2 - (4 - biphenylyl) propanol of the general formula IV

R /r-лR / rl

-СН-СЬ1,-ОН I  -CH-CH1, -ON I

СНэSNE

переводимый при нагревании с тригалогенидом фосфора, например с трибромидом фосфора, в соответствующее соединегае общей формулы 111translated when heated with phosphorus trihalide, for example with phosphorus tribromide, to the corresponding compound of general formula 111

Соединени  общей формулы1 | можно полздшть из замещенных гидратропальдегидов общей формулы VCompounds of general formula1 | It is possible to take half of the substituted hydrate-aldehydes of the general formula V

НH

СН-СCH-S

00

путем восстановлени  боргидридом натри  в растворителе , например в спирте, таком как метанол или этанол. Замещенные гидратропальдегиды общей формулыУ. со своей стороны, синтезируют, например, из эфиров 4 - бифенил - а, (3 эпокси - / метилгидрокоричной кислоты общей формулыby reduction with sodium borohydride in a solvent, for example in an alcohol such as methanol or ethanol. Substituted hydrate-aldehydes of general formula U. for their part, they synthesize, for example, from the esters 4 - biphenyl - a, (3 epoxy - / methyl hydrochloric acid of the general formula

/-Л / -L

/ с -сн-соотг, / with -sn-sootg,

/ / / /

где Rj означает алкильный радикал, посредством нагревани  в спиртовом растворе до температуры кипени  растворител  в присутствии едкого щелока. Соединени  общей формулы VI могут быть получены, в свою очередь, из известных 4 - фенилацетофенонов путем воздействи  эфиром хлоруксусной кислоты в присутствииwhere Rj is an alkyl radical, by heating in an alcohol solution to the boiling point of the solvent in the presence of caustic lye. Compounds of general formula VI can, in turn, be prepared from the known 4-phenylacetophenones by exposure to chloroacetic acid ester in the presence of

амида натри  в бензольном растворе при О-100° С, предпочтительно при 10-20° С.sodium amide in benzene solution at O-100 ° C, preferably at 10-20 ° C.

П р и м е р 1. 3 - (2 - фтор - 4 - бифенилил) масл на  кислота.PRI me R 1. 3 - (2 - fluorine - 4 - biphenylyl) butyric acid.

В суспензию 7,3 г {0,03 моль) 3 - (2 - фтор - 4 бифенилнл ) - 1 - бутанола в 2,4 г (0,04 моль) 85%-ной гидроокиси кали  в 150 мл воды вкапьшают приблизительно при 10° С в течение I час раствор 7,9 г (0,05 моль) перманганата кали  в 60 мл воды.To a suspension of 7.3 g {0.03 mol) 3 - (2 - fluorine - 4 biphenyl) - 1 - butanol in 2.4 g (0.04 mol) of 85% potassium hydroxide in 150 ml of water is dropped at approximately 10 ° C for I hour solution of 7.9 g (0.05 mol) of potassium permanganate in 60 ml of water.

Смесь размещивают 2 час при комнатной температуре и в течение 4 час при 60° С. После охлаждени  отфильтровьшают осадок и дополнительно промывают гор чей водой. Водную, свободную от перманганата составную одеть извлекают эфиром, водныйThe mixture is placed for 2 hours at room temperature and for 4 hours at 60 ° C. After cooling, the precipitate is filtered off and washed with hot water. An aqueous, permanganate-free compound put is extracted with ether;

раствор подкисл ют и путем извлечени  зфиром и этиленхлоридом получают сырую карбоновую кислоту , которую очищают путем хроматографии на силикагеле. После перекристаллизащш из циклогексана шста  3 - (2 - фтор - 4 - бифенилил)the solution is acidified and by extraction with ether and ethylene chloride, the crude carboxylic acid is obtained, which is purified by chromatography on silica gel. After recrystallizing from cyclohexane shsta 3 - (2 - fluorine - 4 - biphenylyl)

масл на  кислота плавитс  при 97-98°С„ .butyric acid melts at 97-98 ° C.

Аналогинно получают следующие соединени : 3- (4- фтор- 4- бифенилил) масл на  кислота,т.пл. 141-143°С (этанол); 3 - (2- хлор- 4- бифенилил)масл на  кислота, т.пл. 128-129° С; 3 - (3 - хлор-4 - бифенилнл) масл на  кислота, т.гш. 106-108° С. П р и м е р 2. Разделение рацемической 3 - (2 фтор - 4 - бифенилил) масл ной кислоты на оптически активные изомеры.The following compounds are prepared analogously: 3- (4-fluoro-4-biphenylyl) butyric acid, m.p. 141-143 ° C (ethanol); 3- (2-chloro-4-biphenylyl) butyric acid, m.p. 128-129 ° C; 3 - (3 - chloro-4 - biphenylnl) butyric acid; 106-108 ° C. Example 2: Separation of racemic 3- (2 fluoro-4-biphenylyl) butyric acid into optically active isomers.

77,5 г (0,3 моль) 3 - (2 - фтор - 4 - бифенилилмасл ной кислоты раствор ют в 1,5л этанола и смешивают с раствором 97,2 г (0,3 моль) хинина в 1,5 л этанола. Получают бесцветный осадок А, который отсасывают, и фильтрат Б. Осадок А 15 раз перекристаллизовьгоают из этанола (всего 30 л)77.5 g (0.3 mol) of 3- (2-fluoro-4-biphenylyl-acid) are dissolved in 1.5 liters of ethanol and mixed with a solution of 97.2 g (0.3 mol) of quinine in 1.5 liters of ethanol A colorless precipitate A is obtained, which is sucked off, and the filtrate B. Sediment A is recrystallized 15 times from ethanol (30 l in total)

причем получают правовращающую3- (2- фтор- 4 - ) масл ную кислоту с т.пл. 87-88°С (из циклогексана), а + 34,5°, выход 5,5 г.moreover, a right rotary 3- (2-fluoro-4-) butyric acid is obtained with a mp. 87-88 ° C (from cyclohexane), and + 34.5 °, yield 5.5 g.

Из фильтрата Б удал ют растворитель и остаток раствор ют гор чим метанолом (500мл). При охлаждении осаждаетс  осадок, который отсасывают и выкидывают. Фильтрат еще 4 раза обрабатывают также метанолом.1 Оставщийс  при вьшариванни метанола остаток раствор ют в 500 мл теплого уксусного эфира и получают при сто нии осадок,The solvent is removed from filtrate B and the residue is dissolved in hot methanol (500 ml). Upon cooling, a precipitate is deposited, which is sucked off and discarded. The filtrate is also treated 4 times with methanol.1 The residue remaining with methanol is dissolved in 500 ml of warm acetic ether and a precipitate is obtained on standing

который отсасывают и перекристаллизовывают приблизительно из 500 мл уксусного эфира.which is sucked off and recrystallized from approximately 500 ml of ethyl acetate.

Получают левовращающую 3 - ( фтор - 4 бифенилил ) масл ную кислоту с т.пл 85-87° С (из циклогексана), cfj- .- 30,5°, выход 2,3 г.A levorotatory 3- (fluorine-4 biphenylyl) butyric acid is obtained with a melting point of 85-87 ° C (from cyclohexane), cfj-30.5 °, yield 2.3 g.

Claims (5)

1. Способ получени  замещенной бифенилмасл ной кислоты общей формулы1. A method for producing substituted biphenylbutyric acid of the general formula Г.Н., G.N., - 2-соон  - 2-soon R - атом галогена, или ее эфиров, или R is a halogen atom, or its ethers, or 5five солей, отличающийс  тем, что спирт общей формулыsalts, characterized in that the alcohol of the general formula CHjCHj CH-CHj-CHj-OHCH-CHj-CHj-OH где R имеет указанное значение, окисл ют с последун цим выделением полученной кислоты в свободном виде или в виде эфира, или в виде соли, или в виде рацематов или в виде оптически активных изомеров.where R has the indicated value, is oxidized, followed by isolation of the resulting acid in free form or as an ester, or as a salt, or as racemates, or as optically active isomers. 2.Оюсоб по п., отличающийс  тем. что процесс ведут прн минус 10 - плюс 80° С.2. Oyusob according to claim. that the process is carried out prn minus 10 - plus 80 ° C. 3.Способ по п. 1, отличающийс  тем, что окисленне ведут перманганатом щелочного металл в нейтральной нлн щелочной среде.3. A method according to claim 1, characterized in that the oxidized lead of the alkali metal permanganate in a neutral nlc alkaline medium. 4. Способ по п. 1,отличающийс  тем, что окисление ведут окисью хрома (1У) в водном растворе или в растворе минеральной кислоты.4. A method according to claim 1, characterized in that the oxidation is carried out with chromium oxide (IV) in an aqueous solution or in a solution of a mineral acid. 5. Способ поп.1, от ли чаю щий с   тем, что окисление ведут хроматом илн бихроматом щелочного ьвталла.5. The method of pop. 1, which means that oxidation is carried out with chromate or dichromate of alkali metal.
SU2069578A 1972-08-17 1974-10-21 Method for preparing substituted biphenylbutyric acid or its esters or salts SU511847A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2240441A DE2240441A1 (en) 1972-08-17 1972-08-17 NEW BIPHENYL DERIVATIVES AND METHOD OF MANUFACTURING

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SU511847A3 true SU511847A3 (en) 1976-04-25

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Family Applications (11)

Application Number Title Priority Date Filing Date
SU1958288A SU484679A3 (en) 1972-08-17 1973-08-15 Method for preparing biphenyl derivatives
SU1958290A SU511846A3 (en) 1972-08-17 1973-08-15 The method of obtaining -biphenylbuttonic acids or their salts
SU1958291A SU482039A3 (en) 1972-08-17 1973-08-15 Method for preparing biphenylyl butenoic acids or their derivatives
SU2069110A SU554810A3 (en) 1972-08-17 1974-10-21 The method of obtaining derivatives of biphenyl or their salts, or racemates, or optically active antipodes
SU2069576A SU561505A3 (en) 1972-08-17 1974-10-21 The method of obtaining 3- (4-biphenylyl) -buttonic acid or its salts
SU7402069575A SU577967A3 (en) 1972-08-17 1974-10-21 Method of preparing substituted biphenylilbutyric acid or its esters,or its amides,or its salts
SU2069578A SU511847A3 (en) 1972-08-17 1974-10-21 Method for preparing substituted biphenylbutyric acid or its esters or salts
SU2069577A SU520907A3 (en) 1972-08-17 1974-10-21 Method for preparing substituted biphenylyl butyric acid or its salt
SU2069774A SU552021A3 (en) 1972-08-17 1974-10-21 The method of obtaining derivatives of biphenyl or their salts
SU2069114A SU538658A3 (en) 1972-08-17 1974-10-21 The method of obtaining biphenylbutyric acids or their salts, or racemates, or optically active antipodes
SU2069771A SU520030A3 (en) 1972-08-17 1974-10-21 Method for preparing substituted biphenylbutyric acid or its ester or its salt

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SU1958288A SU484679A3 (en) 1972-08-17 1973-08-15 Method for preparing biphenyl derivatives
SU1958290A SU511846A3 (en) 1972-08-17 1973-08-15 The method of obtaining -biphenylbuttonic acids or their salts
SU1958291A SU482039A3 (en) 1972-08-17 1973-08-15 Method for preparing biphenylyl butenoic acids or their derivatives
SU2069110A SU554810A3 (en) 1972-08-17 1974-10-21 The method of obtaining derivatives of biphenyl or their salts, or racemates, or optically active antipodes
SU2069576A SU561505A3 (en) 1972-08-17 1974-10-21 The method of obtaining 3- (4-biphenylyl) -buttonic acid or its salts
SU7402069575A SU577967A3 (en) 1972-08-17 1974-10-21 Method of preparing substituted biphenylilbutyric acid or its esters,or its amides,or its salts

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SU2069577A SU520907A3 (en) 1972-08-17 1974-10-21 Method for preparing substituted biphenylyl butyric acid or its salt
SU2069774A SU552021A3 (en) 1972-08-17 1974-10-21 The method of obtaining derivatives of biphenyl or their salts
SU2069114A SU538658A3 (en) 1972-08-17 1974-10-21 The method of obtaining biphenylbutyric acids or their salts, or racemates, or optically active antipodes
SU2069771A SU520030A3 (en) 1972-08-17 1974-10-21 Method for preparing substituted biphenylbutyric acid or its ester or its salt

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CS (3) CS165386B2 (en)
DD (2) DD108071A5 (en)
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ES (4) ES417884A1 (en)
FR (2) FR2196167B1 (en)
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IL (2) IL43004A0 (en)
NL (2) NL7311301A (en)
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FR2457275A1 (en) * 1979-05-21 1980-12-19 Fabre Sa Pierre P-BIPHENYL-4 METHYL-2 BUTEN-3 OIC ACIDS USEFUL IN THE TREATMENT OF RHUMATISMS
RU2686489C1 (en) * 2018-12-27 2019-04-29 Федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургский государственный университет (СПбГУ)" Method of producing α-diazocarbonyl compounds in aqueous medium

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FR2128277B2 (en) * 1970-05-05 1979-06-22 Rorer Inc William H
BE776316R (en) * 1971-03-10 1972-06-06 Rorer Inc William H Phenylacetic acid derivs - as antiinflammatory agents

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BE803734A (en) 1974-02-18
SU554810A3 (en) 1977-04-15
ZA735616B (en) 1976-01-28
ES417884A1 (en) 1976-03-16
DD107901A5 (en) 1974-08-20
SU538658A3 (en) 1976-12-05
FR2196168B1 (en) 1977-02-25
ES417883A1 (en) 1976-11-16
AU476340B2 (en) 1976-09-16
AU5930973A (en) 1975-02-20
IL43004A0 (en) 1973-11-28
ZA735628B (en) 1975-04-30
SU511846A3 (en) 1976-04-25
BG21197A3 (en) 1976-03-20
GB1410852A (en) 1975-10-22
NL7311300A (en) 1974-02-19
DE2240441A1 (en) 1974-02-28
SU552021A3 (en) 1977-03-25
FR2196167B1 (en) 1977-04-15
NL7311301A (en) 1974-02-19
HU166517B (en) 1975-03-28
BG22069A3 (en) 1976-11-25
BG21844A3 (en) 1976-09-20
CS165386B2 (en) 1975-12-22
SU577967A3 (en) 1977-10-25
HU166516B (en) 1975-03-28
AT328427B (en) 1976-03-25
DD108071A5 (en) 1974-09-05
SU561505A3 (en) 1977-06-05
PL90397B1 (en) 1977-01-31
RO62917A (en) 1978-02-15
AU5930873A (en) 1975-02-20
ES432464A1 (en) 1977-02-16
GB1411495A (en) 1975-10-29
JPS49124052A (en) 1974-11-27
AT323144B (en) 1975-06-25
SU520030A3 (en) 1976-06-30
JPS49124051A (en) 1974-11-27
CS165387B2 (en) 1975-12-22
ZA735629B (en) 1976-01-28
SU482039A3 (en) 1975-08-25
BE803733A (en) 1974-02-18
AT323143B (en) 1975-06-25
ES432465A1 (en) 1976-11-16
FR2196167A1 (en) 1974-03-15
RO62918A (en) 1978-04-15
ATA711273A (en) 1975-06-15
CH588435A5 (en) 1977-05-31
SU484679A3 (en) 1975-09-15
SU520907A3 (en) 1976-07-05
BE803732A (en) 1974-02-18
CS165385B2 (en) 1975-12-22
PL94510B1 (en) 1977-08-31
IL43003A0 (en) 1973-11-28
FR2196168A1 (en) 1974-03-15

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