SU518135A3 - Способ получени производных хромана - Google Patents

Способ получени производных хромана

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Publication number
SU518135A3
SU518135A3 SU1978253A SU1978253A SU518135A3 SU 518135 A3 SU518135 A3 SU 518135A3 SU 1978253 A SU1978253 A SU 1978253A SU 1978253 A SU1978253 A SU 1978253A SU 518135 A3 SU518135 A3 SU 518135A3
Authority
SU
USSR - Soviet Union
Prior art keywords
water
ether
tetramethylchroman
washed
solution
Prior art date
Application number
SU1978253A
Other languages
English (en)
Inventor
Соси Гебриэл (Швейцария)
Уэльем Скотт Джон (Сша)
Ричард Парриш Девид (Сша)
Original Assignee
Ф.Гоффманн-Ля Рош И Ко Аг., (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.)
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Application filed by Ф.Гоффманн-Ля Рош И Ко Аг., (Фирма) filed Critical Ф.Гоффманн-Ля Рош И Ко Аг., (Фирма)
Application granted granted Critical
Publication of SU518135A3 publication Critical patent/SU518135A3/ru

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
    • C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • 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
    • 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
    • C07C29/14—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 a —CHO group
    • 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
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
    • C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Emergency Medicine (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Pyrane Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Fats And Perfumes (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Edible Oils And Fats (AREA)

Claims (3)

1000 мл тетрагидрофурана, затем в течение 2,25 ч добавл ют 209,4 г триметилфосфоноацетата . Белую пасту 0,25 ч размешивают, затем добавл ют раствор 132,2 кг (+)-6-aцeтoкcи - 2 - окси - 2,5,7,8 - тетраметилхромана в 1000 мл тетрагидрофурана. Бледно-желтую взвесь 18 ч размешивают при 23°С, после чего 4 ч нагревают с обратным холодильником. Из охлажденных растворов, полученных после двух таких реакций, удал ют растворитель, затем экстрагируют эфиром, промывают водой, сушат сульфатом натри , растворитель удал ют. Получают красно-коричневое масло, содержаш ,ее (±)-метиловый эфир 6-ацетокси-2,5,7,8тетраметилхромап-2-ил в уксусной кислоте. В раствор этого продукта в 2000 мл этанола добавл ют 2000 мл воды и 240 г гидроокиси натри . Раствор 4 ч размешивают при 23°С, промывают нетролейным эфиром (границы кипени  30-60 С), разбавл ют 6000 мл лед ной воды и подкисл ют путем добавлени  но капл м 600 мл концентрированной водой сол ной кислоты в течение 0,5 ч. Твердый продукт отфильтровывают, промывают водой и кристаллизуют из смеси этанолвода , получа  (±)-(6-окси-2,5,7,8-тетраметилхроман-2-ил ) -уксусную кислоту в виде светло-коричневого порошка, т. пл. 168-171°С. Пример 2. В раствор 2-диметиламинометил-3 ,5,6--триметилгидрохинона (полученного из 0,1 мол  триметилгидрохинона) в 120 мл бензола добавл ют 60 мл метакрилонитрила и 2 г гидрохинона. Раствор в атмосфере азота загружают в расплавленном состо нии в стекл нную трубку, 1 ч нагревают до 190°С и охлаждают, промывают 2 н. сол ной кислотой и водой, высушивают сульфатом натри , после чего здал ют растворитель. Темный остаток хроматографируют на 500 г силикагел  со смесью бензола и этилацетата (39:1) и кристаллизуют из смеси эфира и нетролейного эфира (границы кипени  30-60°С), получа  (±)-2-циано-6окси-2 ,5,7,8-тетраметилхроман в виде коричневого порошка, т. пл. 151 - 152°С. Пример 3. Взвесь 2,31 г (±)-2-циано-6 окси-2,5,7,8-тетраметнлхромана в 50 мл 6 н. сол ной кислоты 16 ч нагревают в атмосфере азота с обратным холодильником, затем охлаждают и фильтруют. Твердый продукт промывают водой, высушивают и кристаллизуют из эфира, получа  (±)-6-окси-2,5,7,8-тетраметилхроман-2-карбоновую кислоту, т. пл.-190- 92°С (с разложением). Формула изобретени  I. Способ получени  производных хромана формзлы .:CooK (1) Ri и RI где RI, Ki и Ki - независимо друг от друга , атом водорода или низший алкил, Ra - атом водорода, низший алкил или фенил, п - целое число, равное О или 1, отличаю ш; и и с   тем, что соединение формулы Охп:СНа „ (И) Нг где RI, Ri, Ri, Rg и п имеют указанные значени , R - эфирна  группа и Y - циано-, карбоксигруппа или -COORs-rpynna, где Rs - низший алкил, подвергают гидролизу кислым или щелочным агентом с последуюш;им выделением целевого продукта.
2.Способ по п. 1, отличаюш:ийс  тем, что в качестве кислого агента используют серную или сол ную кислоту.
3.Способ по п. , отличающийс  тем, что в качестве щелочного агента используют гидроокись щелочного металла.
SU1978253A 1972-12-22 1973-12-21 Способ получени производных хромана SU518135A3 (ru)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US31756672A 1972-12-22 1972-12-22

Publications (1)

Publication Number Publication Date
SU518135A3 true SU518135A3 (ru) 1976-06-15

Family

ID=23234257

Family Applications (1)

Application Number Title Priority Date Filing Date
SU1978253A SU518135A3 (ru) 1972-12-22 1973-12-21 Способ получени производных хромана

Country Status (21)

Country Link
JP (3) JPS5946233B2 (ru)
KR (1) KR780000008B1 (ru)
AR (1) AR200751A1 (ru)
AT (1) AT333755B (ru)
BE (2) BE808943A (ru)
CA (1) CA1022562A (ru)
CH (3) CH605892A5 (ru)
DD (1) DD109624A5 (ru)
DE (2) DE2364165A1 (ru)
ES (1) ES421683A1 (ru)
FR (2) FR2284604A1 (ru)
GB (4) GB1456827A (ru)
HU (1) HU168043B (ru)
IE (1) IE38671B1 (ru)
IL (1) IL43888A (ru)
LU (1) LU69067A1 (ru)
NL (2) NL178968C (ru)
PH (1) PH11133A (ru)
SE (1) SE406912B (ru)
SU (1) SU518135A3 (ru)
ZA (1) ZA739471B (ru)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2795497C2 (ru) * 2018-08-17 2023-05-04 Басф Се Синтез производных хроманола

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH618695A5 (en) * 1975-01-27 1980-08-15 Hoffmann La Roche Process for the preparation of chromane derivatives
DE2820861A1 (de) * 1977-05-16 1978-11-23 Hoffmann La Roche Chromanderivate
US4150050A (en) * 1978-01-30 1979-04-17 Hoffmann-La Roche Inc. 3,6-Dioxo-1,4-cyclohexadien-1-yl-butandate esters
DE2861183D1 (en) * 1978-01-30 1981-12-24 Hoffmann La Roche Process for the preparation of chromane derivatives
DE2909601A1 (de) * 1979-03-12 1980-09-25 Basf Ag Verfahren zur herstellung von chromanderivaten
DE3010504A1 (de) * 1980-03-19 1981-10-01 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von 2-hydroxyalkylchromanen
DE3010505A1 (de) * 1980-03-19 1981-10-01 Basf Ag, 6700 Ludwigshafen Chromanderivate, verfahren zu ihrer herstellung, ihre verwendung als stabilisatoren von organischen materialien sowie diese stabilisatoren enthaltende organische materialien
DE3103707A1 (de) * 1981-02-04 1982-08-19 Basf Ag, 6700 Ludwigshafen Chromanderivate
DE3103740A1 (de) * 1981-02-04 1982-08-19 Basf Ag, 6700 Ludwigshafen Chromanderivate
JPS57136582A (en) * 1981-02-19 1982-08-23 Eisai Co Ltd Preparation of optically active alpha-tocopherol
JPS57145871A (en) * 1981-03-05 1982-09-09 Eisai Co Ltd Chromanolcarboxylic derivative
DE3139238A1 (de) * 1981-10-02 1983-04-21 Basf Ag, 6700 Ludwigshafen Optisch aktive bausteine fuer die synthese der seitenkette von (r,r,r)-(alpha)-tocopherol sowie verfahren zu deren herstellung
DE3367391D1 (en) * 1982-12-23 1986-12-11 Ici America Inc Chroman compounds
ZA844519B (en) * 1983-06-24 1985-02-27 Hoffmann La Roche Dihydrobenzopyran derivatives
DE3760058D1 (en) * 1986-01-23 1989-04-13 Hoffmann La Roche 3,4-dihydro-2,5,7,8-tetramethyl-2h-1-benzopyran derivatives and processes for their preparation
US4987231A (en) * 1989-08-04 1991-01-22 Pfizer Inc. Optical resolution method for 3R-(3-carboxybenzyl)-6-(5-fluoro-2-benzothiazolyl)methoxy-4R-chromanol
CA2082004A1 (en) * 1991-11-20 1993-05-21 David Laffan Substituted pentaalkylchromans
DE19859251A1 (de) * 1998-12-22 2000-06-29 Basf Ag Verfahren zur Herstellung von substituierten Chromanderivaten
WO2002012221A1 (fr) * 2000-08-03 2002-02-14 Kuraray Co., Ltd. Procede de resolution optique de l'acide (±)-6-hydroxy-2,5,7,8,-tetramethyle de coumarone-2-carboxylique
EP1710239A4 (en) * 2004-01-30 2009-03-18 Mitsubishi Gas Chemical Co PROCESS FOR PRODUCING A CHROMIUM COMPOUND
KR101233223B1 (ko) * 2004-12-21 2013-02-14 제이엔씨 석유 화학 주식회사 크로만환을 가지는 액정 화합물, 액정 조성물 및 이 액정조성물을 함유하는 액정 표시소자
EP2522647B1 (en) * 2011-05-10 2014-04-30 DSM IP Assets B.V. Process of separating chiral isomers of chroman compounds and their derivatives and precursors
NL2010010C2 (en) 2012-12-19 2014-06-23 Sulfateq B V Compounds for protection of cells.
EP4108658A4 (en) * 2020-02-21 2024-05-22 Sumitomo Pharma Co., Ltd. OPTICALLY RESOLVED TROLOX INTERMEDIATE AND PRODUCTION METHOD THEREFOR

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2795497C2 (ru) * 2018-08-17 2023-05-04 Басф Се Синтез производных хроманола

Also Published As

Publication number Publication date
JPS4988876A (ru) 1974-08-24
AU6400973A (en) 1975-07-03
IE38671B1 (en) 1978-05-10
IE38671L (en) 1974-06-22
JPS59144780A (ja) 1984-08-18
FR2284604B1 (ru) 1979-05-11
CH603617A5 (ru) 1978-08-31
IL43888A (en) 1977-02-28
HU168043B (ru) 1976-02-28
NL7317587A (ru) 1974-06-25
PH11133A (en) 1977-10-27
BE808942A (fr) 1974-06-21
LU69067A1 (ru) 1975-08-20
CH605892A5 (ru) 1978-10-13
ES421683A1 (es) 1976-04-01
ATA1076973A (de) 1976-04-15
CH622257A5 (en) 1981-03-31
BE808943A (fr) 1974-06-21
IL43888A0 (en) 1974-03-14
DD109624A5 (ru) 1974-11-12
FR2284604A1 (fr) 1976-04-09
AT333755B (de) 1976-12-10
NL178968C (nl) 1986-06-16
FR2255299A1 (ru) 1975-07-18
JPS6026795B2 (ja) 1985-06-25
JPS5946233B2 (ja) 1984-11-10
GB1456827A (en) 1976-11-24
AR200751A1 (es) 1974-12-13
DE2364141A1 (de) 1974-06-27
FR2255299B1 (ru) 1977-06-10
ZA739471B (en) 1974-08-28
SE406912B (sv) 1979-03-05
GB1456828A (en) 1976-11-24
CA1022562A (en) 1977-12-13
JPS4988877A (ru) 1974-08-24
KR780000008B1 (en) 1978-03-04
GB1456830A (en) 1976-11-24
DE2364165A1 (de) 1974-06-27
NL7317590A (ru) 1974-06-25
GB1456829A (en) 1976-11-24

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