SU471710A3 - Способ получени 4-/4-бифенилил/1-бутанола - Google Patents

Способ получени 4-/4-бифенилил/1-бутанола

Info

Publication number
SU471710A3
SU471710A3 SU1955028A SU1955028A SU471710A3 SU 471710 A3 SU471710 A3 SU 471710A3 SU 1955028 A SU1955028 A SU 1955028A SU 1955028 A SU1955028 A SU 1955028A SU 471710 A3 SU471710 A3 SU 471710A3
Authority
SU
USSR - Soviet Union
Prior art keywords
biphenylyl
butanol
obtaining
over
formula
Prior art date
Application number
SU1955028A
Other languages
English (en)
Inventor
Зеегер Эрнст
Энгель Вольфганг
Тойфель Гельмут
Энгельхардт 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.)
Filing date
Publication date
Application filed by Д-Р Карл Томэ Гмбх (Фирма) filed Critical Д-Р Карл Томэ Гмбх (Фирма)
Application granted granted Critical
Publication of SU471710A3 publication Critical patent/SU471710A3/ru

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/09Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/10Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
    • C07C29/103Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/17Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/60Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by elimination of -OH groups, e.g. by dehydration
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/18Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
    • C07C33/24Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part polycyclic without condensed ring systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/26Polyhydroxylic alcohols containing only six-membered aromatic rings as cyclic part

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pain & Pain Management (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Rheumatology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

(54) СПОСОБ ПОЛУЧЕНИЯ 4-(4-БИФЕНИЛИЛ)-1-БУТАНОЛА
1
Р1зобретение относитс  к области получени  спиртов, а именно 4-(4-бифенилил)-1-бутанола , который  вл етс  биологически активным соединением и может найти применение в фармацевтической промышленност.
При осуществлении предложенного способа , использу  известную реакцию органической химии - восстановление г; дроксильной груипы, получают новое ие описанное в литературе соединение - 4-(4-бифенилил)-1бутанол формулы 1, обладающее улучшенными фармакологическими свойствами,
,,-сн,он
Сущность способа состоит в тол;, что соединение формулы 2
CH-CHj-CK -CH OH
он
восстанавливают каталитически активированным водородом.
В качестве катализатора примен ют катализаторы из благородного металла, предпочтительно палладий на животном угле. Восстановление провод т при температуре О-100° С, предпочтительно при комнатио температуре, при давлении водорода 1 - 100 атм, предпочтительно 3-10 атм, и в npi;сутствии растворител , например спирта, эф)ь ра карбоновой кислоты или низших карбоновых кислот. Повое соединение формулы . можно также получать путем гидрироваии т соединени  общей формулы 2 в присутствии окиси меди (хрома или окиси цинка) в качестве катализатора при телиюратуре 150- 300° С и давлении водорода 150-300 ог.и.
Исходные соединени  общей формулы 2 известны или их можно получать известными способами.
Бутилеигликоль формулы 2 получают, нппример , путем восстановлени  4-(4-бифенилил )-4-оксомасл ной кислоты с помощью алюмогидрида лити  или борана натри  вирисутствии безводного хлорида алюмини  при комнатной температуре в присутствии растворител , например диметокснэтана.
Примеи емуЕо в качестве исходного соединени  4-(4-бифенилил)-4-оксомасл ную кислоту или ее эфиры можно получать путем реакции взаимодействи  бифенила с ангидридом  нтарной к слоты или галоидангидридом кислого эфира  нтарной кислоты в присутствии кислоты Льюиса, например безводного хлорида алюмини , в растворителе, иапример нитробензоле или метилеих.юриде, ири температуре О-80° С.
При м е р. 4-(4-бифенилил)-1-бутанол.
9,68 г (0,04 моль} 1-(4-бифенилил)-1,4-бутилекгликол  (т. пл. 79-80° С) раствор ют в 100 мл метаиола, добавл ют 1 г паллади  иа угле в качеетве катализатора и гидрируют при комнатной температуре и давлении 5 атм, пока не будет поглощено рассчитанное количество водорода. Затем отсасывают от катализатора, дистиллируют растворитель из фильтрата, ири этом получают твердый остаток, который перекристаллизовывают из петролейного эфира и небольшого количества уксусного эфира. Получают 8,32 г (93% от теоретического) бесцветных кристаллов 4-(4-бифенилил)-1-бутаиола с т. пл. 75-76° С.
Предмет изобретени  1. Способ получеии  4-(4-бифеиилил)-1бутанола , отличающийс  тем, что соединение формулы
сн-сн,-сн,-сн.,он
// //
Iг г г
ОН
каталитически восстанавливают водородом присутствии растворител 
последующим выделением целевого иродукта известными ириемами.
2.Способ ио п. 1, отличающийс  тем, что в качестве катализатора иримен ют палладий иа угле.
3.Способ по пи. 1 и 2, отличающийс  тем, что восстановление провод т при комнатной температуре иод давлением водорода 3-10 атм.
SU1955028A 1971-10-15 1972-10-12 Способ получени 4-/4-бифенилил/1-бутанола SU471710A3 (ru)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2151312A DE2151312C3 (de) 1971-10-15 1971-10-15 4- (4-Biphen ylyl) -l-butanol

Publications (1)

Publication Number Publication Date
SU471710A3 true SU471710A3 (ru) 1975-05-25

Family

ID=5822378

Family Applications (7)

Application Number Title Priority Date Filing Date
SU1955030A SU464106A3 (ru) 1971-10-15 1972-10-12 Способ получени 4-(4-бифенилил)1 -бутанола
SU1957826A SU474968A3 (ru) 1971-10-15 1972-10-12 Способ получени 4-(4-бифенилил)1-бутанола
SU1955028A SU471710A3 (ru) 1971-10-15 1972-10-12 Способ получени 4-/4-бифенилил/1-бутанола
SU1839112A SU453823A3 (ru) 1971-10-15 1972-10-12 Способ получения 4-
SU1955026A SU464105A3 (ru) 1971-10-15 1972-10-12 Способ получени 4-(4-бифенилил)-1 бутанола
SU1955347A SU496713A3 (ru) 1971-10-15 1973-08-23 Способ получени 4-(2-бифенилил)1-бутанола
SU1955029A SU496714A3 (ru) 1971-10-15 1973-08-23 Способ получени 4-(4-бифенилил)1-бутанола

Family Applications Before (2)

Application Number Title Priority Date Filing Date
SU1955030A SU464106A3 (ru) 1971-10-15 1972-10-12 Способ получени 4-(4-бифенилил)1 -бутанола
SU1957826A SU474968A3 (ru) 1971-10-15 1972-10-12 Способ получени 4-(4-бифенилил)1-бутанола

Family Applications After (4)

Application Number Title Priority Date Filing Date
SU1839112A SU453823A3 (ru) 1971-10-15 1972-10-12 Способ получения 4-
SU1955026A SU464105A3 (ru) 1971-10-15 1972-10-12 Способ получени 4-(4-бифенилил)-1 бутанола
SU1955347A SU496713A3 (ru) 1971-10-15 1973-08-23 Способ получени 4-(2-бифенилил)1-бутанола
SU1955029A SU496714A3 (ru) 1971-10-15 1973-08-23 Способ получени 4-(4-бифенилил)1-бутанола

Country Status (28)

Country Link
US (1) US3801654A (ru)
JP (3) JPS5320031B2 (ru)
AT (7) AT327177B (ru)
AU (1) AU469279B2 (ru)
BE (1) BE790086A (ru)
BG (5) BG20777A3 (ru)
CA (1) CA993897A (ru)
CH (4) CH589575A5 (ru)
CS (7) CS160609B2 (ru)
DD (1) DD103233A5 (ru)
DE (1) DE2151312C3 (ru)
DK (1) DK129573B (ru)
ES (5) ES407583A1 (ru)
FI (1) FI55984C (ru)
FR (1) FR2157860B1 (ru)
GB (1) GB1361574A (ru)
HU (1) HU164696B (ru)
IE (1) IE36775B1 (ru)
IL (1) IL40571A (ru)
NL (1) NL7213927A (ru)
NO (1) NO136092C (ru)
PH (1) PH13645A (ru)
PL (4) PL83601B1 (ru)
RO (8) RO70060A (ru)
SE (2) SE399417B (ru)
SU (7) SU464106A3 (ru)
YU (5) YU255972A (ru)
ZA (1) ZA727320B (ru)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4053639A (en) * 1964-01-24 1977-10-11 The Boots Company Limited Therapeutically active phenylalkane derivatives
BE790085A (fr) * 1971-10-15 1973-04-13 Thomae Gmbh Dr K Nouveaux 4-(4-biphenylyl)-butanols
DE2240438A1 (de) * 1972-08-17 1974-02-28 Thomae Gmbh Dr K Neue 2-(4-biphenylyl)-tetrahydrofurane und verfahren zu ihrer herstellung
DE2240440A1 (de) * 1972-08-17 1974-02-28 Thomae Gmbh Dr K Neue (4-biphenylyl)-alkohole und verfahren zu ihrer herstellung
DE2341506A1 (de) * 1973-08-16 1975-02-27 Thomae Gmbh Dr K Neue biphenylderivate und verfahren zu ihrer herstellung
DE2528958A1 (de) * 1975-06-28 1977-01-13 Merck Patent Gmbh Araliphatische dihalogenverbindungen und verfahren zu ihrer herstellung
DE2708520A1 (de) * 1977-02-26 1978-08-31 Thomae Gmbh Dr K Neue arzneimittelkombinationen und verfahren zu ihrer herstellung
DE3001303A1 (de) * 1980-01-16 1981-07-23 Basf Ag, 6700 Ludwigshafen Optisch aktive phenylpropan-derivate, ihre herstellung und verwendung
AT399471B (de) * 1993-06-04 1995-05-26 Ifw Manfred Otte Ges M B H & C Spritzgiessform

Also Published As

Publication number Publication date
CS160615B2 (ru) 1975-03-28
ES415241A1 (es) 1976-06-16
AT315823B (de) 1974-06-10
FI55984B (fi) 1979-07-31
BG20332A3 (ru) 1975-11-05
NO136092C (no) 1977-07-20
AU469279B2 (en) 1976-02-12
BG20560A3 (ru) 1975-12-05
IL40571A (en) 1975-10-15
CH575358A5 (ru) 1976-05-14
SU496714A3 (ru) 1975-12-25
DD103233A5 (ru) 1974-01-12
CH599082A5 (ru) 1978-05-12
BE790086A (fr) 1973-04-13
SE7600800L (sv) 1976-01-26
BG19586A3 (ru) 1975-06-25
NL7213927A (ru) 1973-04-17
AT321901B (de) 1975-04-25
RO70058A (ro) 1982-09-09
PL91407B1 (ru) 1977-02-28
GB1361574A (en) 1974-07-30
RO71307A (ro) 1982-03-24
US3801654A (en) 1974-04-02
SU453823A3 (ru) 1974-12-15
AU4774872A (en) 1974-04-26
SU464105A3 (ru) 1975-03-15
YU197179A (en) 1982-06-18
SU496713A3 (ru) 1975-12-25
JPS5387341A (en) 1978-08-01
PL83601B1 (ru) 1975-12-31
SU464106A3 (ru) 1975-03-15
AT321898B (de) 1975-04-25
ES415242A1 (es) 1976-06-16
DE2151312B2 (ru) 1974-11-28
FR2157860A1 (ru) 1973-06-08
AT327177B (de) 1976-01-26
JPS5515448B2 (ru) 1980-04-23
SE399417B (sv) 1978-02-13
AT321899B (de) 1975-04-25
IL40571A0 (en) 1972-12-29
RO71244A (ro) 1982-07-06
CA993897A (en) 1976-07-27
AT321900B (de) 1975-04-25
RO71306A (ro) 1981-08-17
ATA573873A (de) 1975-04-15
CH589575A5 (ru) 1977-07-15
BG20777A3 (ru) 1975-12-20
YU197479A (en) 1982-06-18
IE36775L (en) 1973-04-15
DK129573C (ru) 1975-03-24
YU197379A (en) 1982-06-18
HU164696B (ru) 1974-03-28
CS160609B2 (ru) 1975-03-28
BG20333A3 (ru) 1975-11-05
DE2151312C3 (de) 1975-07-31
PH13645A (en) 1980-08-18
SU474968A3 (ru) 1975-06-25
RO70059A (ro) 1980-03-15
ES407583A1 (es) 1975-11-01
YU197279A (en) 1982-06-18
CS160614B2 (ru) 1975-03-28
PL91408B1 (ru) 1977-02-28
CS160610B2 (ru) 1975-03-28
CS160611B2 (ru) 1975-03-28
FR2157860B1 (ru) 1975-10-31
RO70567A (ro) 1981-07-30
CS160613B2 (ru) 1975-03-28
JPS5320031B2 (ru) 1978-06-24
DK129573B (da) 1974-10-28
JPS4861459A (ru) 1973-08-28
NO136092B (ru) 1977-04-12
ES415243A1 (es) 1976-11-01
PL91409B1 (ru) 1977-02-28
DE2151312A1 (de) 1973-04-19
YU255972A (en) 1982-06-18
RO69378A (ro) 1981-04-20
JPS5542054B2 (ru) 1980-10-28
ZA727320B (en) 1974-06-26
JPS5387342A (en) 1978-08-01
FI55984C (fi) 1979-11-12
CS160612B2 (ru) 1975-03-28
ES415244A1 (es) 1976-11-01
RO70060A (ro) 1981-06-30
AT321897B (de) 1975-04-25
CH590185A5 (ru) 1977-07-29
IE36775B1 (en) 1977-02-16

Similar Documents

Publication Publication Date Title
Christian Jr et al. Derivatives of γ-Valerolactone, 1, 4-Pentanediol and 1, 4-Di-(β-cyanoethoxy)-pentane1
SU471710A3 (ru) Способ получени 4-/4-бифенилил/1-бутанола
Gardner et al. Reaction of phenolic Mannich base methiodides and oxides with various nucleophiles
US2607805A (en) Hydrogenation of glycolic acid to ethylene glycol
MX167628B (es) Derivado del acido quinolin carboxilico
US3188319A (en) Production of vinyl estess
Wolfrom et al. Crystalline xylitol
Yamamoto et al. Cleavage of esters under nearly neutral conditions at high pressure. Chemo-and regioselective hydrolysis in organic solvents
Lee et al. REARRANGEMENT STUDIES WITH C14: V. THE SOLVOLYSIS OF 2-PHENYLETHYL-1-C14 p-TOLUENESULPHONATE
US2516826A (en) Process for catalytic semihydrogenation of tertiary acetylenic monohydric alcohols
Barton et al. 356. The constitution of sedanolide
Williams et al. Identification of Amides through the Mercury Derivatives
Young The Reaction of Ketene with Unsaturated Ketones
Chandler et al. Synthetical Applications of Activated Metal Catalysts. XVII. The Hydrogenolysis of Aromatic Ethers by Raney Nickel
US3232996A (en) Purification of butynediol
DE2834168C2 (de) Verfahren zur Herstellung von 2-(2-Hydroxyäthoxy)äthyl-N-(α,α,α-trifluor-m-tolyl)anthranilat
Blomquist et al. The Reaction of Ketene with Organic Halogen Compounds1
DE3122562C1 (de) Verfahren zur Herstellung von D-(+)-Biotin
US2796431A (en) 6-hydroxy and 7-hydroxy derivatives of 1, 4alpha- dimethylperhydrophenanthrene-1-carboxylic acid
US2963488A (en) 2-aceto-3, 4-furandimethanol and esters
FUSON et al. Condensation of Benzalacetophenone with Phenylmagnesium Bromide. 2-Benzhydryl-2-hydroxy-3, 3-diphenylpropionic Acid1
US2975191A (en) Reduction of i
US4990682A (en) Process for the preparation of 5-chloro-2-pentanone
US3055936A (en) Nitroalkanoic acids and esters thereof
US2377571A (en) Method of preparing transquinitol diacetate