GB1456828A - Chromane derivatives - Google Patents

Chromane derivatives

Info

Publication number
GB1456828A
GB1456828A GB5929873A GB5929873A GB1456828A GB 1456828 A GB1456828 A GB 1456828A GB 5929873 A GB5929873 A GB 5929873A GB 5929873 A GB5929873 A GB 5929873A GB 1456828 A GB1456828 A GB 1456828A
Authority
GB
United Kingdom
Prior art keywords
formula
hydroxy group
halide
compound
chromane
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB5929873A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1456828A publication Critical patent/GB1456828A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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)
  • Edible Oils And Fats (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Fats And Perfumes (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)

Abstract

1456828 Chromane derivatives F HOFFMANN-LA ROCHE & CO AG 21 Dec 1973 [22 Dec 1972] 59298/73 Headings C2C and C2P Novel chromane derivatives of Formula I wherein R represents a hydroxy group or an ether group convertible into a hydroxy group by hydrolysis or hydrogenolysis or an ester group convertible into a hydroxy group by hydrolysis, R 1 represents a C 1 -C 7 alkyl group and m stands for zero or 1, are prepared by reacting a compound of Formula II with a phosphorane of Formula III where R 2 , R 3 and R 4 are aryl groups, or with a phosphonate of Formula IV where R 5 and R 6 are aryloxy or C 1 -C 7 alkoxy to give a chromane derivative of Formula IA or by treating a compound of Formula II with an alkali metal cyanide, converting the resulting compound of Formula V into a chromane derivative of Formula IB<SP>1</SP> where R<SP>11</SP> represents a hydroxy group or an ether group convertible into a hydroxy group by hydrolysis or hydrogenolysis, by treatment of the compound V with an anhydrous mineral acid in a lower alkanol, addition of water to the product, and subsequent treatment with a Lewis acid, and converting by esterification a hydroxy group denoted by R<SP>11</SP> in Formula IB<SP>1</SP>, if desired, into an ester group to yield a chromane derivative of the general Formula IB The chromane derivatives of Formula I may be transformed into alphatocopheral via an acid halide of Formula VII where X is a halogen atom, or via an aldehyde of Formula VIII by a metal organic condensation with a compound of Formula XI wherein Z represents Li or MgX (X representing a halogen atom) and n stands for zero or 1 with the proviso that the sum of m and n in Formulµ VII and XI or VIII and XI is 1, or via an aldehyde of the general Formula VIII shown above by a phospho-organic condensation with a halide of the Formula X where X is a halogen atom an n is 0 or 1 with the proviso that the sum of m and n is Formula VIII and x is 1, and converting the obtained alphatocopherol precursor into alphatocopherol in a manner known per se. The halide of Formula X used in the phospho-organic condensation may be converted into a phosphorane of formula in which R 2 , R 3 and R 4 are aryl by reaction with a phosphine of formula to produce a phosphonium salt, followed by treatment with base. Alternatively the halide may be converted into a phosphonate of formula by reaction with a phosphite of Formula in which R 5 , R 6 and R 7 are aryloxy or C 1 -C 7 alkoxy. The halide of Formula X may be prepared by dehydrating 7R,11R-phytol, treating the resulting product with ozone gas to produce various ozonides, followed by reduction with a complex metal hydride to produce of mixture of isomers of Formula IXA which may be separated by fractional distillation, and halogenation of the products. The alcohols of Formula IXA may also be prepared by reducing the corresponding aldehyde.
GB5929873A 1972-12-22 1973-12-21 Chromane derivatives Expired GB1456828A (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number Publication Date
GB1456828A true GB1456828A (en) 1976-11-24

Family

ID=23234257

Family Applications (4)

Application Number Title Priority Date Filing Date
GB5929873A Expired GB1456828A (en) 1972-12-22 1973-12-21 Chromane derivatives
GB2227175A Expired GB1456829A (en) 1972-12-22 1973-12-21 Chromane derivatives
GB5929673A Expired GB1456827A (en) 1972-12-22 1973-12-21 Chromane derivatives
GB2227275A Expired GB1456830A (en) 1972-12-22 1973-12-21 Substituted undecanes

Family Applications After (3)

Application Number Title Priority Date Filing Date
GB2227175A Expired GB1456829A (en) 1972-12-22 1973-12-21 Chromane derivatives
GB5929673A Expired GB1456827A (en) 1972-12-22 1973-12-21 Chromane derivatives
GB2227275A Expired GB1456830A (en) 1972-12-22 1973-12-21 Substituted undecanes

Country Status (21)

Country Link
JP (3) JPS4988876A (en)
KR (1) KR780000008B1 (en)
AR (1) AR200751A1 (en)
AT (1) AT333755B (en)
BE (2) BE808942A (en)
CA (1) CA1022562A (en)
CH (3) CH605892A5 (en)
DD (1) DD109624A5 (en)
DE (2) DE2364165A1 (en)
ES (1) ES421683A1 (en)
FR (2) FR2284604A1 (en)
GB (4) GB1456828A (en)
HU (1) HU168043B (en)
IE (1) IE38671B1 (en)
IL (1) IL43888A (en)
LU (1) LU69067A1 (en)
NL (2) NL178968C (en)
PH (1) PH11133A (en)
SE (1) SE406912B (en)
SU (1) SU518135A3 (en)
ZA (1) ZA739471B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0411813A1 (en) * 1989-08-04 1991-02-06 Pfizer Inc. Optical resolution method for 3S-(3-carboxybenzyl)-6-(5-fluoro-2-benzothiazolyl)methoxy-4S-chromanol

Families Citing this family (23)

* 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
NL7805217A (en) * 1977-05-16 1978-11-20 Hoffmann La Roche PROCESS FOR THE PREPARATION OF INTERMEDIATE COMPOUNDS FOR THE PREPARATION OF VITAMIN E.
EP0003484B1 (en) * 1978-01-30 1981-10-14 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Process for the preparation of chromane derivatives
US4150050A (en) * 1978-01-30 1979-04-17 Hoffmann-La Roche Inc. 3,6-Dioxo-1,4-cyclohexadien-1-yl-butandate esters
DE2909601A1 (en) * 1979-03-12 1980-09-25 Basf Ag METHOD FOR PRODUCING CHROME DERIVATIVES
DE3010505A1 (en) * 1980-03-19 1981-10-01 Basf Ag, 6700 Ludwigshafen CHROME DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, THEIR USE AS STABILIZERS OF ORGANIC MATERIALS AND ORGANIC MATERIALS CONTAINING THESE STABILIZERS
DE3010504A1 (en) * 1980-03-19 1981-10-01 Basf Ag, 6700 Ludwigshafen METHOD FOR THE PRODUCTION OF 2-HYDROXYALKYLCHROMANS
DE3103707A1 (en) * 1981-02-04 1982-08-19 Basf Ag, 6700 Ludwigshafen CHROME DERIVATIVES
DE3103740A1 (en) 1981-02-04 1982-08-19 Basf Ag, 6700 Ludwigshafen CHROME DERIVATIVES
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 (en) * 1981-10-02 1983-04-21 Basf Ag, 6700 Ludwigshafen OPTICALLY ACTIVE COMPONENTS FOR THE SYNTHESIS OF THE SIDE CHAIN OF (R, R, R) - (ALPHA) -TOCOPHEROL AND METHOD FOR THE PRODUCTION THEREOF
ATE23337T1 (en) * 1982-12-23 1986-11-15 Ici America Inc CHROMAN CONNECTIONS.
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
CA2082004A1 (en) * 1991-11-20 1993-05-21 David Laffan Substituted pentaalkylchromans
DE19859251A1 (en) * 1998-12-22 2000-06-29 Basf Ag Process for the preparation of substituted chroman derivatives
WO2002012221A1 (en) * 2000-08-03 2002-02-14 Kuraray Co., Ltd. Method for optical resolution of (±)-6-hydroxy-2,5,7,8-tetramethylcoumarone-2-carboxylic acid
JP4904816B2 (en) * 2004-01-30 2012-03-28 三菱瓦斯化学株式会社 Method for producing chroman compound
KR101233223B1 (en) * 2004-12-21 2013-02-14 제이엔씨 석유 화학 주식회사 Liquid crystal compound having a chroman ring, liquid crystal composition, and liquid crystal display device comprising the liquid crystal composition
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.
WO2021167095A1 (en) * 2020-02-21 2021-08-26 大日本住友製薬株式会社 Optically resolved trolox intermediate and method for producing same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0411813A1 (en) * 1989-08-04 1991-02-06 Pfizer Inc. Optical resolution method for 3S-(3-carboxybenzyl)-6-(5-fluoro-2-benzothiazolyl)methoxy-4S-chromanol

Also Published As

Publication number Publication date
JPS59144780A (en) 1984-08-18
FR2255299B1 (en) 1977-06-10
GB1456827A (en) 1976-11-24
CA1022562A (en) 1977-12-13
LU69067A1 (en) 1975-08-20
KR780000008B1 (en) 1978-03-04
DD109624A5 (en) 1974-11-12
AR200751A1 (en) 1974-12-13
JPS5946233B2 (en) 1984-11-10
FR2284604B1 (en) 1979-05-11
CH605892A5 (en) 1978-10-13
IE38671B1 (en) 1978-05-10
AU6400973A (en) 1975-07-03
JPS6026795B2 (en) 1985-06-25
NL7317587A (en) 1974-06-25
DE2364141A1 (en) 1974-06-27
JPS4988876A (en) 1974-08-24
IL43888A (en) 1977-02-28
BE808943A (en) 1974-06-21
JPS4988877A (en) 1974-08-24
DE2364165A1 (en) 1974-06-27
SE406912B (en) 1979-03-05
HU168043B (en) 1976-02-28
ATA1076973A (en) 1976-04-15
ES421683A1 (en) 1976-04-01
AT333755B (en) 1976-12-10
SU518135A3 (en) 1976-06-15
CH603617A5 (en) 1978-08-31
BE808942A (en) 1974-06-21
FR2284604A1 (en) 1976-04-09
IL43888A0 (en) 1974-03-14
NL7317590A (en) 1974-06-25
ZA739471B (en) 1974-08-28
GB1456830A (en) 1976-11-24
NL178968C (en) 1986-06-16
IE38671L (en) 1974-06-22
FR2255299A1 (en) 1975-07-18
CH622257A5 (en) 1981-03-31
PH11133A (en) 1977-10-27
GB1456829A (en) 1976-11-24

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee