BE840103A - Procede de cyclisation des alcools gamma-delta, delta epsilon insatures et produits obtenus par ce procede - Google Patents

Procede de cyclisation des alcools gamma-delta, delta epsilon insatures et produits obtenus par ce procede

Info

Publication number: BE840103A
Authority: BE; Belgium
Prior art keywords: emi; resin; delta; cyclized; alcohols
Prior art date: 1975-03-27

Application number

BE165622A

Other languages

English (en)

French (fr)

Inventor

A Prevedello

M Brunelli

E Platone

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.)

1975-03-27

Filing date

1976-03-26

Publication date

1976-09-27

1976-03-26 Application filed filed Critical

1976-09-27 Publication of BE840103A publication Critical patent/BE840103A/fr

Links

238000000034 method Methods 0.000 title claims description 27
230000008569 process Effects 0.000 title claims description 23
150000001298 alcohols Chemical class 0.000 title description 12
230000001351 cycling effect Effects 0.000 title 1
239000011347 resin Substances 0.000 claims description 34
229920005989 resin Polymers 0.000 claims description 34
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 24
230000015572 biosynthetic process Effects 0.000 claims description 21
230000003197 catalytic effect Effects 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
238000003786 synthesis reaction Methods 0.000 claims description 9
125000002091 cationic group Chemical group 0.000 claims description 8
AFWHMVTTYMQCQP-UHFFFAOYSA-N 2-(2-methyl-5-propan-2-yloxolan-2-yl)acetonitrile Chemical compound CC(C)C1CCC(C)(CC#N)O1 AFWHMVTTYMQCQP-UHFFFAOYSA-N 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 6
LKZJNXXGMPYNJN-UHFFFAOYSA-N 3-hydroxy-3,7-dimethyloct-6-enenitrile Chemical compound CC(C)=CCCC(C)(O)CC#N LKZJNXXGMPYNJN-UHFFFAOYSA-N 0.000 claims description 5
239000003729 cation exchange resin Substances 0.000 claims description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
JSCDRQIEVSNCBE-UHFFFAOYSA-N 2-(2,6,6-trimethyloxan-2-yl)acetonitrile Chemical compound CC1(C)CCCC(C)(CC#N)O1 JSCDRQIEVSNCBE-UHFFFAOYSA-N 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
150000002500 ions Chemical class 0.000 claims description 3
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
238000005342 ion exchange Methods 0.000 claims 1
USXILEVHWYGLKS-UHFFFAOYSA-N oct-6-enenitrile Chemical compound CC=CCCCCC#N USXILEVHWYGLKS-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 description 16
238000007363 ring formation reaction Methods 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
238000004817 gas chromatography Methods 0.000 description 8
239000003456 ion exchange resin Substances 0.000 description 7
229920003303 ion-exchange polymer Polymers 0.000 description 7
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000008096 xylene Substances 0.000 description 6
239000000243 solution Substances 0.000 description 5
150000003527 tetrahydropyrans Chemical class 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000008901 benefit Effects 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000001793 charged compounds Chemical class 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
238000007865 diluting Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
-1 terpene alcohols Chemical class 0.000 description 2
150000003509 tertiary alcohols Chemical class 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
241001331845 Equus asinus x caballus Species 0.000 description 1
241000208152 Geranium Species 0.000 description 1
NRSISXVNIZMPKF-UHFFFAOYSA-N OC(CC#N)CCC=CC Chemical compound OC(CC#N)CCC=CC NRSISXVNIZMPKF-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
150000001243 acetic acids Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000009471 action Effects 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000000484 citronellol Nutrition 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000007547 defect Effects 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
239000003599 detergent Substances 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012262 resinous product Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
125000001412 tetrahydropyranyl group Chemical class 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1

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
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Fats And Perfumes (AREA)
Furan Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

BE165622A 1975-03-27 1976-03-26 Procede de cyclisation des alcools gamma-delta, delta epsilon insatures et produits obtenus par ce procede BE840103A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT2172475A IT1037201B (it)	1975-03-27	1975-03-27	Procedimento per la ciclizzazione di alcooli gamma delta o delta epsilon insaturi e prodotti cosi ottenuti

Publications (1)

Publication Number	Publication Date
BE840103A true BE840103A (fr)	1976-09-27

Family

ID=11185955

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE165622A BE840103A (fr)	1975-03-27	1976-03-26	Procede de cyclisation des alcools gamma-delta, delta epsilon insatures et produits obtenus par ce procede

Country Status (5)

Country	Link
AT (1)	AT352719B (de)
BE (1)	BE840103A (de)
HU (1)	HU179105B (de)
IT (1)	IT1037201B (de)
ZA (1)	ZA761741B (de)

1975
- 1975-03-27 IT IT2172475A patent/IT1037201B/it active
1976
- 1976-03-22 ZA ZA761741A patent/ZA761741B/xx unknown
- 1976-03-26 AT AT225576A patent/AT352719B/de not_active IP Right Cessation
- 1976-03-26 BE BE165622A patent/BE840103A/fr not_active IP Right Cessation
- 1976-03-26 HU HU76AI254A patent/HU179105B/hu unknown

Also Published As

Publication number	Publication date
IT1037201B (it)	1979-11-10
ZA761741B (en)	1977-03-30
HU179105B (en)	1982-08-28
ATA225576A (de)	1979-03-15
AT352719B (de)	1979-10-10

Legal Events

Date

Code

Title

Description

1984-09-30

RE

Patent lapsed

Owner name: ANIC S.P.A.

Effective date: 19840326

Publication	Publication Date	Title
EP0283364B1 (de)	1991-01-09	Mono- oder Diester von Endoethano-9,10-dihydro-9,10-anthracen-dicarboxy-11,11-säure, Verfahren zur Herstellung und Anwendung um symmetrische oder asymmetrische Methyliden-Malonate herzustellen
EP0597069B1 (de)	1998-08-12	Enzymatisches Verfahren zur Herstellung von n-Hexanal, 3-(Z)-Hexen-1-al, 2-(E)-hexen-1-al, oder entsprechenden Alkoholen mittels einer Soja-Lipoxygenase und einer Guave-Lyase
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EP0378825B1 (de)	1994-07-06	Alicyclische Ester und ihre Anwendung als Riechstoffkomponenten
BE840103A (fr)	1976-09-27	Procede de cyclisation des alcools gamma-delta, delta epsilon insatures et produits obtenus par ce procede
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EP0013995B1 (de)	1982-12-29	Verfahren zur Herstellung acetylenischer macrocyclischer Ketone
FR2582648A1 (fr)	1986-12-05	Intermediaires carbacycline optiquement actifs et procedes de leur preparation
CH644341A5 (fr)	1984-07-31	Composes tricycliques hydroxyles et leur utilisation en tant qu'ingredients parfumants.
EP0012390B1 (de)	1982-11-24	Verfahren zur Herstellung von Muscon und Pyran-Zwischenprodukte
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EP0579991B1 (de)	1998-09-16	Verfahren zur Herstellung eines bicyclischen Decalinketons
EP0563346B1 (de)	1997-02-26	Verfahren zur Herstellung von Karbonsäuren mit Hilfe von Mikroorganismen
EP0216659B1 (de)	1989-03-08	Dihalogen-2,2-vinylhalogenformiate, ihr Herstellungsverfahren und ihre Anwendungen
CH629468A5 (fr)	1982-04-30	Composes alicycliques insatures, leur utilisation a titre d'ingredients parfumants et procede pour leur preparation.
CH640496A5 (fr)	1984-01-13	Procede pour la preparation de beta-damascenone.
FR2605314A1 (fr)	1988-04-22	Procede pour la fabrication de l'acide beta-hydroxybutyrique et de ses sels par hydrolyse d'oligomeres de l'acide beta-hydroxybutyrique en milieu basique.
FR2486526A1 (fr)	1982-01-15	Procede de preparation de derives de l'oxyde de diphenyle
CH284404A (fr)	1952-07-31	Procédé de préparation d'une lactone macrocyclique.
EP0177742A2 (de)	1986-04-16	Stickstoff-Verbindungen, ihre Herstellung und Verwendung als Ausgangsprodukte zur Herstellung von Decalinketonen
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