SU471710A3 - Способ получени 4-/4-бифенилил/1-бутанола - Google Patents
Способ получени 4-/4-бифенилил/1-бутанолаInfo
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation 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
- C07C29/103—Preparation 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation 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
- C07C29/136—Preparation 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
- C07C29/143—Preparation 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation 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
- C07C29/136—Preparation 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
- C07C29/147—Preparation 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation 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
- C07C29/136—Preparation 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
- C07C29/147—Preparation 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
- C07C29/149—Preparation 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/60—Preparation 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/18—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
- C07C33/24—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part polycyclic without condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/26—Polyhydroxylic 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.
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)
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 |
-
0
- BE BE790086D patent/BE790086A/xx not_active IP Right Cessation
-
1971
- 1971-10-15 DE DE2151312A patent/DE2151312C3/de not_active Expired
-
1972
- 1972-09-22 SE SE7212263A patent/SE399417B/xx unknown
- 1972-10-04 US US00294940A patent/US3801654A/en not_active Expired - Lifetime
- 1972-10-05 AT AT573873*7A patent/AT327177B/de not_active IP Right Cessation
- 1972-10-05 AT AT573673A patent/AT321897B/de not_active IP Right Cessation
- 1972-10-05 AT AT852372A patent/AT315823B/de not_active IP Right Cessation
- 1972-10-05 AT AT573573A patent/AT321898B/de not_active IP Right Cessation
- 1972-10-05 AT AT573473A patent/AT321899B/de not_active IP Right Cessation
- 1972-10-05 AT AT573373A patent/AT321901B/de not_active IP Right Cessation
- 1972-10-05 AT AT573773A patent/AT321900B/de not_active IP Right Cessation
- 1972-10-06 PH PH13983A patent/PH13645A/en unknown
- 1972-10-11 DD DD166149A patent/DD103233A5/xx unknown
- 1972-10-12 YU YU02559/72A patent/YU255972A/xx unknown
- 1972-10-12 SU SU1955030A patent/SU464106A3/ru active
- 1972-10-12 SU SU1957826A patent/SU474968A3/ru active
- 1972-10-12 SU SU1955028A patent/SU471710A3/ru active
- 1972-10-12 SU SU1839112A patent/SU453823A3/ru active
- 1972-10-12 SU SU1955026A patent/SU464105A3/ru active
- 1972-10-13 BG BG23546A patent/BG20777A3/xx unknown
- 1972-10-13 BG BG21617A patent/BG20560A3/xx unknown
- 1972-10-13 PL PL1972158243A patent/PL83601B1/pl unknown
- 1972-10-13 CS CS6922A patent/CS160609B2/cs unknown
- 1972-10-13 CS CS5229*[A patent/CS160613B2/cs unknown
- 1972-10-13 CA CA153,847A patent/CA993897A/en not_active Expired
- 1972-10-13 BG BG23543A patent/BG19586A3/xx unknown
- 1972-10-13 NL NL7213927A patent/NL7213927A/xx not_active Application Discontinuation
- 1972-10-13 PL PL1972173621A patent/PL91407B1/pl unknown
- 1972-10-13 GB GB4744272A patent/GB1361574A/en not_active Expired
- 1972-10-13 CH CH63676A patent/CH589575A5/xx not_active IP Right Cessation
- 1972-10-13 BG BG23545A patent/BG20333A3/xx unknown
- 1972-10-13 JP JP10314872A patent/JPS5320031B2/ja not_active Expired
- 1972-10-13 ZA ZA727320A patent/ZA727320B/xx unknown
- 1972-10-13 NO NO3683/72A patent/NO136092C/no unknown
- 1972-10-13 CS CS5231*[A patent/CS160615B2/cs unknown
- 1972-10-13 CS CS5230*[A patent/CS160614B2/cs unknown
- 1972-10-13 FR FR7236362A patent/FR2157860B1/fr not_active Expired
- 1972-10-13 CH CH1500072A patent/CH575358A5/xx not_active IP Right Cessation
- 1972-10-13 CS CS5226*[A patent/CS160610B2/cs unknown
- 1972-10-13 HU HUTO891A patent/HU164696B/hu unknown
- 1972-10-13 DK DK506872AA patent/DK129573B/da not_active IP Right Cessation
- 1972-10-13 IL IL40571A patent/IL40571A/xx unknown
- 1972-10-13 CH CH72676A patent/CH590185A5/xx not_active IP Right Cessation
- 1972-10-13 ES ES407583A patent/ES407583A1/es not_active Expired
- 1972-10-13 IE IE1394/72A patent/IE36775B1/xx unknown
- 1972-10-13 PL PL1972173620A patent/PL91409B1/pl unknown
- 1972-10-13 FI FI2841/72A patent/FI55984C/fi active
- 1972-10-13 CS CS5227*[A patent/CS160611B2/cs unknown
- 1972-10-13 AU AU47748/72A patent/AU469279B2/en not_active Expired
- 1972-10-13 PL PL1972173619A patent/PL91408B1/pl unknown
- 1972-10-13 BG BG23544A patent/BG20332A3/xx unknown
- 1972-10-13 CS CS5228*[A patent/CS160612B2/cs unknown
- 1972-10-15 RO RO7283157A patent/RO70060A/ro unknown
- 1972-10-15 RO RO7283159A patent/RO71306A/ro unknown
- 1972-10-15 RO RO7283156A patent/RO69378A/ro unknown
- 1972-10-15 RO RO7283154A patent/RO70059A/ro unknown
- 1972-10-15 RO RO7283160A patent/RO71307A/ro unknown
- 1972-10-15 RO RO7283155A patent/RO70567A/ro unknown
- 1972-10-16 RO RO7283153A patent/RO70058A/ro unknown
- 1972-10-16 RO RO7272524A patent/RO71244A/ro unknown
-
1973
- 1973-05-26 ES ES415242A patent/ES415242A1/es not_active Expired
- 1973-05-26 ES ES415241A patent/ES415241A1/es not_active Expired
- 1973-05-26 ES ES415244A patent/ES415244A1/es not_active Expired
- 1973-05-26 ES ES415243A patent/ES415243A1/es not_active Expired
- 1973-08-23 SU SU1955347A patent/SU496713A3/ru active
- 1973-08-23 SU SU1955029A patent/SU496714A3/ru active
-
1976
- 1976-01-26 SE SE7600800A patent/SE7600800L/xx unknown
- 1976-04-29 CH CH206977A patent/CH599082A5/xx not_active IP Right Cessation
-
1977
- 1977-09-09 JP JP10868477A patent/JPS5387342A/ja active Granted
- 1977-09-09 JP JP10868377A patent/JPS5387341A/ja active Granted
-
1979
- 1979-08-13 YU YU01974/79A patent/YU197479A/xx unknown
- 1979-08-13 YU YU01973/79A patent/YU197379A/xx unknown
- 1979-08-13 YU YU01971/79A patent/YU197179A/xx unknown
- 1979-08-13 YU YU01972/79A patent/YU197279A/xx unknown
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