BE852918A - Procede de cyclisation du dehydrolinalol et produits obtenus - Google Patents
Procede de cyclisation du dehydrolinalol et produits obtenusInfo
- Publication number
- BE852918A BE852918A BE176155A BE176155A BE852918A BE 852918 A BE852918 A BE 852918A BE 176155 A BE176155 A BE 176155A BE 176155 A BE176155 A BE 176155A BE 852918 A BE852918 A BE 852918A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- cyclization
- dhl
- polyphosphoric acid
- dehydrolinalool
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 230000001351 cycling effect Effects 0.000 title 1
- 239000001371 (5E)-3,5-dimethylocta-1,5,7-trien-3-ol Substances 0.000 claims description 27
- ZJIQIJIQBTVTDY-SREVYHEPSA-N dehydrolinalool Chemical compound CC(=C)\C=C/CC(C)(O)C=C ZJIQIJIQBTVTDY-SREVYHEPSA-N 0.000 claims description 27
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 24
- 238000007363 ring formation reaction Methods 0.000 claims description 9
- 230000003197 catalytic effect Effects 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- XSDYMDMXNRPZHU-UHFFFAOYSA-N 2-ethynyl-2,6,6-trimethyloxane Chemical compound CC1(C)CCCC(C)(C#C)O1 XSDYMDMXNRPZHU-UHFFFAOYSA-N 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 6
- JIYZCVGAWRMUDR-UHFFFAOYSA-N 1-(3,3-dimethylcyclohexen-1-yl)ethanone Chemical compound CC(=O)C1=CC(C)(C)CCC1 JIYZCVGAWRMUDR-UHFFFAOYSA-N 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 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 6
- 235000019253 formic acid Nutrition 0.000 description 6
- 238000011068 loading method Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ZKTKNSXLODIMFZ-UHFFFAOYSA-N 2-ethynyloxane Chemical compound C#CC1CCCCO1 ZKTKNSXLODIMFZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- NETOHYFTCONTDT-UHFFFAOYSA-N linaloyl oxide Chemical compound CC1(C)CCCC(C)(C=C)O1 NETOHYFTCONTDT-UHFFFAOYSA-N 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 241000755716 Convallaria Species 0.000 description 1
- 235000009046 Convallaria majalis Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 238000000926 separation method 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
- 239000000758 substrate Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- 238000005406 washing Methods 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/543—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings to a six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2158176A IT1058547B (it) | 1976-03-26 | 1976-03-26 | Procedimento di ciclizzazione del deidrolinalolo e prodotti ottenuti con tale procedimento |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE852918A true BE852918A (fr) | 1977-07-18 |
Family
ID=11183902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE176155A BE852918A (fr) | 1976-03-26 | 1977-03-25 | Procede de cyclisation du dehydrolinalol et produits obtenus |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE852918A (it) |
| IT (1) | IT1058547B (it) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5234902A (en) * | 1992-07-28 | 1993-08-10 | International Flavors & Fragrances Inc. | Compositions containing high proportion of alpha,3,3-trimethyl-1-cyclohexen-1-methanol derivative, organoleptic uses thereof and process for preparing same |
| EP1186600A1 (en) * | 2000-09-06 | 2002-03-13 | Roche Vitamins AG | Process for the preparation of substituted pyranes |
| US6455707B1 (en) | 2000-09-06 | 2002-09-24 | Roche Vitamins, Inc. | Process for the preparation of substitued pyranes |
| WO2014083121A1 (en) | 2012-11-28 | 2014-06-05 | Dsm Ip Assets B. V. | Synthesis of tetrahydromyrcenol |
| CN104341284A (zh) * | 2014-06-27 | 2015-02-11 | 深圳波顿香料有限公司 | 一种1-(5,5-二甲基-1-环己烯-1-基)-4-戊烯-1-酮的制备方法 |
| WO2016128423A1 (en) * | 2015-02-10 | 2016-08-18 | Dsm Ip Assets B.V. | Process of production of cyclo-dehydrolinalool (ii) |
| WO2016128422A1 (en) * | 2015-02-10 | 2016-08-18 | Dsm Ip Assets B.V. | Process of production of cyclo-dehydrolinalool (i) |
| CN107406405A (zh) * | 2014-12-18 | 2017-11-28 | V.马内菲尔斯 | 新的1‑(3,3‑二甲基环己‑1‑烯基)乙酮的缩醛、其制备方法以及其在香料中的用途 |
-
1976
- 1976-03-26 IT IT2158176A patent/IT1058547B/it active
-
1977
- 1977-03-25 BE BE176155A patent/BE852918A/fr not_active IP Right Cessation
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5234902A (en) * | 1992-07-28 | 1993-08-10 | International Flavors & Fragrances Inc. | Compositions containing high proportion of alpha,3,3-trimethyl-1-cyclohexen-1-methanol derivative, organoleptic uses thereof and process for preparing same |
| US5276176A (en) * | 1992-07-28 | 1994-01-04 | International Flavors & Fragrances Inc. | Compositions containing high proportion of alpha,3,3-trimethyl-1-cylclohexen-1-methanol derivative, organoleptic uses thereof and process for preparing same |
| EP1186600A1 (en) * | 2000-09-06 | 2002-03-13 | Roche Vitamins AG | Process for the preparation of substituted pyranes |
| US6455707B1 (en) | 2000-09-06 | 2002-09-24 | Roche Vitamins, Inc. | Process for the preparation of substitued pyranes |
| CN100418961C (zh) * | 2000-09-06 | 2008-09-17 | Dsmip资产有限公司 | 取代吡喃的制备方法 |
| WO2014083121A1 (en) | 2012-11-28 | 2014-06-05 | Dsm Ip Assets B. V. | Synthesis of tetrahydromyrcenol |
| CN104341284A (zh) * | 2014-06-27 | 2015-02-11 | 深圳波顿香料有限公司 | 一种1-(5,5-二甲基-1-环己烯-1-基)-4-戊烯-1-酮的制备方法 |
| CN107406405A (zh) * | 2014-12-18 | 2017-11-28 | V.马内菲尔斯 | 新的1‑(3,3‑二甲基环己‑1‑烯基)乙酮的缩醛、其制备方法以及其在香料中的用途 |
| WO2016128423A1 (en) * | 2015-02-10 | 2016-08-18 | Dsm Ip Assets B.V. | Process of production of cyclo-dehydrolinalool (ii) |
| WO2016128422A1 (en) * | 2015-02-10 | 2016-08-18 | Dsm Ip Assets B.V. | Process of production of cyclo-dehydrolinalool (i) |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1058547B (it) | 1982-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Patent lapsed |
Owner name: ANIC S.P.A. Effective date: 19850325 |