SE8200519L - MANUFACTURE OF OLD PYRONS - Google Patents

MANUFACTURE OF OLD PYRONS

Info

Publication number
SE8200519L
SE8200519L SE8200519A SE8200519A SE8200519L SE 8200519 L SE8200519 L SE 8200519L SE 8200519 A SE8200519 A SE 8200519A SE 8200519 A SE8200519 A SE 8200519A SE 8200519 L SE8200519 L SE 8200519L
Authority
SE
Sweden
Prior art keywords
gamma
alkyl
pyrones
pyrons
old
Prior art date
Application number
SE8200519A
Other languages
Swedish (sv)
Other versions
SE445042B (en
Inventor
T M Brennan
D P Brannegan
P D Weeks
D E Kuhla
Original Assignee
Pfizer
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
Priority claimed from US05/721,885 external-priority patent/US4082717A/en
Application filed by Pfizer filed Critical Pfizer
Publication of SE8200519L publication Critical patent/SE8200519L/en
Publication of SE445042B publication Critical patent/SE445042B/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrane Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Cosmetics (AREA)
  • Saccharide Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Furan Compounds (AREA)
  • Transforming Electric Information Into Light Information (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Picture Signal Circuits (AREA)
  • Processing Of Color Television Signals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Control Of El Displays (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Seasonings (AREA)

Abstract

The gamma-pyrones of formula I in which the symbols have the meaning given in Claim 1 are obtained by a simple and economic "one-pot" process by reaction of a furfuryl alcohol of formula III with at least 2 equivalents of a halogenated oxidising agent, in aqueous solution at a temperature of between -50 DEG and +50 DEG C, and then the reaction mixture is heated until hydrolysis of the intermediate formed is virtually complete. The gamma-pyrones obtained can be used as products which enhance flavour and fragrance in food and cosmetic preparations.

Claims (1)

PATENTERAVPATENTERAV 1. FOrfarande for framstallning av en gamma-pyron, som her formeln van i R Sr vate oiler alkyl med 1-4 kolatomer och R"' betecknar vate slier alkyl med 1-4 kolatomer,kannetecknat darav, att en forening, corn har formeln (21)Ans n Rotel (51 )Klass (74)0mbud NY US P Branneg )01d Lyme, (I) en ekvivalent av en halogenhaltig oxidant utvald bland klor, brom, bromklerid, hypoklorsyrlighet, hypobromsyrlighet eller en blandning darav och att reaktionsblandningen upphettas tills hydrolys av del erhallna 4-halo-dihydropyranintermedlatet Sr vasentligen fullstandig. r 8200519-0 8068 C 07 D WOO Branns an 3)P D 2)Pawcatuk, (IV) R'OR van i R och 12'" har oven angiven betydelse och 12' Sr vate, alkyl med 1-4 Soarer eller -CO" van i R" Sr metyl, etyl oiler fenyl, briatt reageravattenlosning mod minstA process for the preparation of a gamma-pyrone, in which the formula used in R 1r represents hydrogen or alkyl having 1-4 carbon atoms and R (21) Ans n Rotel (51) Class (74) 0mbud NY US P Branneg) 01d Lyme, (I) an equivalent of a halogenated oxidant selected from chlorine, bromine, bromochloride, hypochlorous acid, hypobromic acid or a mixture thereof and heating the reaction mixture until hydrolysis of the partially obtained 4-halo-dihydropyran intermediate Sr is substantially complete. 12 'Sr vate, alkyl with 1-4 Soar or -CO "van in R" Sr methyl, ethyl or phenyl, brittle reaction water solution against at least
SE8200519A 1976-08-02 1982-01-29 PROCEDURE FOR MANUFACTURING GAMMA PYRONS SE445042B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US71090176A 1976-08-02 1976-08-02
US05/721,885 US4082717A (en) 1976-08-02 1976-09-09 Preparation of gamma-pyrones

Publications (2)

Publication Number Publication Date
SE8200519L true SE8200519L (en) 1982-01-29
SE445042B SE445042B (en) 1986-05-26

Family

ID=27108548

Family Applications (6)

Application Number Title Priority Date Filing Date
SE7707035A SE433079B (en) 1976-08-02 1977-06-16 PROCEDURE FOR MANUFACTURING V-PYRONS
SE8200521A SE452616B (en) 1976-08-02 1982-01-29 PROCEDURE FOR PREPARATION OF 4-HALO-2H-PYRANE-3 (6H) -ON COMPOUNDS
SE8200520A SE444564B (en) 1976-08-02 1982-01-29 4-HALOGENE DIHYDROPYRANE COMPOUNDS FOR USE AS INTERMEDIATE IN THE PREPARATION OF GAMMA PYRONS AND PROCEDURE FOR PREPARING THEREOF
SE8200519A SE445042B (en) 1976-08-02 1982-01-29 PROCEDURE FOR MANUFACTURING GAMMA PYRONS
SE8200518A SE445041B (en) 1976-08-02 1982-01-29 PROCEDURE FOR MANUFACTURING GAMMA PYRONS
SE8200522A SE444565B (en) 1976-08-02 1982-01-29 6,6'-OXIBIS / 4-HALO-2H-PYRANE-3 (6H) -ON / COMPOUNDS FOR USE AS INTERMEDIATE IN THE PREPARATION OF GAMMA PYRONS AND PROCEDURE FOR PREPARING THEREOF

Family Applications Before (3)

Application Number Title Priority Date Filing Date
SE7707035A SE433079B (en) 1976-08-02 1977-06-16 PROCEDURE FOR MANUFACTURING V-PYRONS
SE8200521A SE452616B (en) 1976-08-02 1982-01-29 PROCEDURE FOR PREPARATION OF 4-HALO-2H-PYRANE-3 (6H) -ON COMPOUNDS
SE8200520A SE444564B (en) 1976-08-02 1982-01-29 4-HALOGENE DIHYDROPYRANE COMPOUNDS FOR USE AS INTERMEDIATE IN THE PREPARATION OF GAMMA PYRONS AND PROCEDURE FOR PREPARING THEREOF

Family Applications After (2)

Application Number Title Priority Date Filing Date
SE8200518A SE445041B (en) 1976-08-02 1982-01-29 PROCEDURE FOR MANUFACTURING GAMMA PYRONS
SE8200522A SE444565B (en) 1976-08-02 1982-01-29 6,6'-OXIBIS / 4-HALO-2H-PYRANE-3 (6H) -ON / COMPOUNDS FOR USE AS INTERMEDIATE IN THE PREPARATION OF GAMMA PYRONS AND PROCEDURE FOR PREPARING THEREOF

Country Status (36)

Country Link
JP (7) JPS5318578A (en)
AR (1) AR216080A1 (en)
AT (3) AT362790B (en)
BE (1) BE855965A (en)
BG (4) BG28989A4 (en)
BR (1) BR7703970A (en)
CA (3) CA1095921A (en)
CH (4) CH625798A5 (en)
CS (3) CS203921B2 (en)
DD (1) DD132494A5 (en)
DE (3) DE2760221C2 (en)
DK (4) DK153483C (en)
EG (1) EG13080A (en)
ES (5) ES459994A1 (en)
FI (6) FI72722C (en)
FR (1) FR2372821A1 (en)
GB (5) GB1538371A (en)
GR (1) GR68938B (en)
HK (5) HK30581A (en)
HU (4) HU186026B (en)
IE (5) IE45642B1 (en)
IT (1) IT1106258B (en)
LU (1) LU77600A1 (en)
MX (1) MX4597E (en)
MY (3) MY8100287A (en)
NL (5) NL170955C (en)
NO (7) NO150561C (en)
NZ (1) NZ184342A (en)
PH (5) PH13557A (en)
PL (4) PL115586B1 (en)
PT (1) PT66694B (en)
RO (4) RO78953A (en)
SE (6) SE433079B (en)
SU (2) SU955859A3 (en)
TR (1) TR19652A (en)
YU (4) YU40166B (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1095921A (en) * 1976-08-02 1981-02-17 Thomas M. Brennan Preparation of gamma-pyrones
JPS5444675A (en) * 1977-09-12 1979-04-09 Shin Etsu Chem Co Ltd Production of 3-hydroxy-4-pyrone analog
FR2402654A1 (en) * 1977-09-12 1979-04-06 Shinetsu Chemical Co Tetra:hydro-pyranone derivs. - useful as intermediates for cpds. used as food flavours
JPS5741226U (en) * 1980-08-20 1982-03-05
JPS59135008U (en) * 1983-02-28 1984-09-10 松下電工株式会社 Distribution board device
JPS6050245A (en) * 1983-08-29 1985-03-19 Nissan Motor Co Ltd Fuel injection device in internal-combustion engine
JPH0226945Y2 (en) * 1985-09-11 1990-07-20
JP2586607B2 (en) * 1987-10-30 1997-03-05 日産化学工業株式会社 Production method of optically active alcohol
CA2681545C (en) 2007-03-28 2013-10-01 Apotex Technologies Inc. Fluorinated derivatives of deferiprone
PL2268282T3 (en) 2008-04-25 2015-04-30 Apotex Tech Inc Liquid formulation for deferiprone with palatable taste
ME01911B (en) 2009-07-03 2014-12-20 Apotex Tech Inc Fluorinated derivatives of 3-hydroxypyridin-4-ones
WO2017168309A1 (en) * 2016-03-29 2017-10-05 Dr. Reddy’S Laboratories Limited Process for preparation of eribulin and intermediates thereof
CN108609456B (en) * 2016-12-13 2021-03-12 奥的斯电梯公司 Openable expansion panel and elevator suspended ceiling, elevator car and elevator system with same
CN111606879A (en) * 2020-05-25 2020-09-01 安徽金禾实业股份有限公司 One-pot method for preparing 2-hydroxymethyl-3-alkoxy-4H-pyran-4-one

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3491122A (en) * 1966-09-14 1970-01-20 Monsanto Co Synthesis of 4-pyrones
US3547912A (en) * 1968-07-29 1970-12-15 American Home Prod Derivatives of 2h-pyran-3(6h)-ones and preparation thereof
JPS5145565B1 (en) * 1968-10-12 1976-12-04
US3621063A (en) * 1968-12-24 1971-11-16 Monsanto Co Unsaturated acyclic ketones
US3832357A (en) * 1971-05-26 1974-08-27 Daicel Ltd Process for preparation of 3-hydroxy-2-alkyl-4-pyrone
JPS5212166A (en) * 1975-07-17 1977-01-29 Tatsuya Shono Process for preparation of 4-pyron derivatives
IE42789B1 (en) * 1975-08-28 1980-10-22 Pfizer Preparation of gamma-pyrones
CA1095921A (en) * 1976-08-02 1981-02-17 Thomas M. Brennan Preparation of gamma-pyrones

Also Published As

Publication number Publication date
HU186026B (en) 1985-05-28
FI831702A0 (en) 1983-05-16
DK153483C (en) 1988-11-28
DK326086A (en) 1986-07-09
CS203923B2 (en) 1981-03-31
PH15185A (en) 1982-09-10
SU955859A3 (en) 1982-08-30
FI831701A0 (en) 1983-05-16
ES470746A1 (en) 1979-01-16
NL182805C (en) 1988-05-16
NO821847L (en) 1978-02-03
ES470745A1 (en) 1979-01-16
JPS5436271A (en) 1979-03-16
NO821850L (en) 1978-02-03
CH625798A5 (en) 1981-10-15
SU1015826A3 (en) 1983-04-30
FI831701L (en) 1983-05-16
DK326086D0 (en) 1986-07-09
NO821848L (en) 1978-02-03
YU270382A (en) 1983-10-31
FI72723C (en) 1987-07-10
NO150043B (en) 1984-04-30
JPS5814433B2 (en) 1983-03-18
NO772193L (en) 1978-02-03
IE45645B1 (en) 1982-10-20
FI831704L (en) 1983-05-16
CA1095921A (en) 1981-02-17
GB1538374A (en) 1979-01-17
HU185686B (en) 1985-03-28
NO150561B (en) 1984-07-30
BG29136A3 (en) 1980-09-15
BG28849A3 (en) 1980-07-15
CA1117541A (en) 1982-02-02
SE445042B (en) 1986-05-26
NL182476C (en) 1988-03-16
NO151365B (en) 1984-12-17
FI72721C (en) 1987-07-10
FI831704A0 (en) 1983-05-16
DK325986A (en) 1986-07-09
AU2601777A (en) 1978-09-21
YU42613B (en) 1988-10-31
PL115586B1 (en) 1981-04-30
IE45643B1 (en) 1982-10-20
RO78953A (en) 1982-04-12
SE8200518L (en) 1982-01-29
NO150043C (en) 1984-08-15
CA1110254A (en) 1981-10-06
YU146977A (en) 1983-06-30
NL8105538A (en) 1982-04-01
JPS5618596B2 (en) 1981-04-30
NO150559C (en) 1984-11-07
NO821851L (en) 1978-02-03
NO150560B (en) 1984-07-30
FI72720B (en) 1987-03-31
DK325986D0 (en) 1986-07-09
JPS5436267A (en) 1979-03-16
HK30381A (en) 1981-07-10
HK30581A (en) 1981-07-10
IE45644B1 (en) 1982-10-20
AT362790B (en) 1981-06-10
BE855965A (en) 1977-12-21
PT66694A (en) 1977-07-01
BG28989A4 (en) 1980-08-15
IE790584L (en) 1978-02-02
ES470743A1 (en) 1979-01-16
GB1538375A (en) 1979-01-17
MX4597E (en) 1982-06-25
FI73424B (en) 1987-06-30
JPS5436269A (en) 1979-03-16
JPS5729034B2 (en) 1982-06-19
HU180040B (en) 1983-01-28
IE790586L (en) 1978-02-02
HK30781A (en) 1981-07-10
FI831703L (en) 1983-05-16
YU274782A (en) 1983-12-31
FR2372821B1 (en) 1980-10-17
ES459994A1 (en) 1978-11-16
RO78951A2 (en) 1982-04-12
NL8105537A (en) 1982-04-01
JPS5436270A (en) 1979-03-16
SE433079B (en) 1984-05-07
RO74367A (en) 1981-11-24
PL215006A1 (en) 1979-12-17
SE452616B (en) 1987-12-07
FI831702L (en) 1983-05-16
DK154079B (en) 1988-10-10
GB1538371A (en) 1979-01-17
FI73424C (en) 1987-10-09
NO150042C (en) 1984-08-15
NL170955B (en) 1982-08-16
SE8200520L (en) 1982-01-29
JPS5318578A (en) 1978-02-20
CH626357A5 (en) 1981-11-13
NO150042B (en) 1984-04-30
AT363470B (en) 1981-08-10
DK153401B (en) 1988-07-11
DE2760220C2 (en) 1987-08-20
SE444564B (en) 1986-04-21
TR19652A (en) 1979-09-17
FI831700A0 (en) 1983-05-16
PL115496B1 (en) 1981-04-30
NL182477B (en) 1987-10-16
NL182805B (en) 1987-12-16
PL215008A1 (en) 1979-12-17
ATA124480A (en) 1981-01-15
MY8100262A (en) 1981-12-31
DK153401C (en) 1988-11-28
PH13557A (en) 1980-06-26
MY8100267A (en) 1981-12-31
DK276177A (en) 1978-02-03
NZ184342A (en) 1978-09-25
GB1538373A (en) 1979-01-17
DE2760221C2 (en) 1989-10-05
NL182478B (en) 1987-10-16
FI72722C (en) 1987-07-10
FI72722B (en) 1987-03-31
SE8200521L (en) 1982-01-29
NO150561C (en) 1984-11-07
EG13080A (en) 1981-03-31
IT1106258B (en) 1985-11-11
NO150559B (en) 1984-07-30
SE8200522L (en) 1982-01-29
PL199798A1 (en) 1979-08-27
DE2728499C2 (en) 1986-04-03
IE45641L (en) 1978-02-02
IE790585L (en) 1978-02-02
FI72723B (en) 1987-03-31
ES470744A1 (en) 1979-01-16
FI72119B (en) 1986-12-31
HK30681A (en) 1981-07-10
PL215007A1 (en) 1979-12-17
PH13874A (en) 1980-10-24
SE445041B (en) 1986-05-26
NO834236L (en) 1978-02-03
IE45642B1 (en) 1982-10-20
JPS5420500B2 (en) 1979-07-23
DK153484B (en) 1988-07-18
DK154079C (en) 1989-02-27
NO151365C (en) 1985-03-27
CS203922B2 (en) 1981-03-31
NL182478C (en) 1988-03-16
CS203921B2 (en) 1981-03-31
DK326186D0 (en) 1986-07-09
HU185687B (en) 1985-03-28
PL115497B1 (en) 1981-04-30
CH625235A5 (en) 1981-09-15
RO78952A (en) 1982-04-12
FI831703A0 (en) 1983-05-16
NO821849L (en) 1978-02-03
IE45641B1 (en) 1982-10-20
DK153483B (en) 1988-07-18
DE2728499A1 (en) 1978-02-09
FI72720C (en) 1987-07-10
NL182477C (en) 1988-03-16
FI72721B (en) 1987-03-31
NL8105540A (en) 1982-04-01
PH13926A (en) 1980-11-04
SE444565B (en) 1986-04-21
ATA440477A (en) 1980-11-15
AT364356B (en) 1981-10-12
AR216080A1 (en) 1979-11-30
NO150560C (en) 1984-11-07
IE790587L (en) 1978-02-02
DK326186A (en) 1986-07-09
DD132494A5 (en) 1978-10-04
JPS5436268A (en) 1979-03-16
PH14625A (en) 1981-10-12
GR68938B (en) 1982-03-29
YU166383A (en) 1986-02-28
HK30481A (en) 1981-07-10
NL182476B (en) 1987-10-16
MY8100287A (en) 1981-12-31
YU43190B (en) 1989-04-30
GB1538372A (en) 1979-01-17
NL8105539A (en) 1982-04-01
YU40166B (en) 1985-08-31
JPS5618597B2 (en) 1981-04-30
PT66694B (en) 1978-11-17
FR2372821A1 (en) 1978-06-30
FI831700L (en) 1983-05-16
NL7706811A (en) 1978-02-06
ATA124380A (en) 1981-03-15
FI72119C (en) 1987-04-13
DK153484C (en) 1988-11-28
NL170955C (en) 1983-01-17
BG28988A4 (en) 1980-08-15
LU77600A1 (en) 1978-02-01
FI771934A7 (en) 1978-02-03
JPS5436266A (en) 1979-03-16
BR7703970A (en) 1978-07-04
CH626358A5 (en) 1981-11-13
SE7707035L (en) 1978-02-03

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