CA1055529A - Preparation of terpenophenols - Google Patents
Preparation of terpenophenolsInfo
- Publication number
- CA1055529A CA1055529A CA224,571A CA224571A CA1055529A CA 1055529 A CA1055529 A CA 1055529A CA 224571 A CA224571 A CA 224571A CA 1055529 A CA1055529 A CA 1055529A
- Authority
- CA
- Canada
- Prior art keywords
- dans
- est
- formule
- produit
- terpenophenols
- 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
Links
- 238000002360 preparation method Methods 0.000 title abstract description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 10
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 230000017858 demethylation Effects 0.000 abstract 1
- 238000010520 demethylation reaction Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 235000007586 terpenes Nutrition 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 241000655872 Puia Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 240000004543 Vicia ervilia Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- -1 des phenols Chemical class 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/42—Halogenated derivatives containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oncology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB16142/74A GB1510302A (en) | 1974-04-11 | 1974-04-11 | Terpenophenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1055529A true CA1055529A (en) | 1979-05-29 |
Family
ID=10071943
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA224,571A Expired CA1055529A (en) | 1974-04-11 | 1975-04-11 | Preparation of terpenophenols |
| CA224,583A Expired CA1045164A (fr) | 1974-04-11 | 1975-04-11 | Procede de preparation de nouveaux terpenophenols |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA224,583A Expired CA1045164A (fr) | 1974-04-11 | 1975-04-11 | Procede de preparation de nouveaux terpenophenols |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4067899A (en, 2012) |
| JP (2) | JPS5830289B2 (en, 2012) |
| BE (1) | BE827797A (en, 2012) |
| CA (2) | CA1055529A (en, 2012) |
| CH (2) | CH593891A5 (en, 2012) |
| DE (1) | DE2515382A1 (en, 2012) |
| DK (2) | DK142170B (en, 2012) |
| FR (1) | FR2267093B1 (en, 2012) |
| GB (1) | GB1510302A (en, 2012) |
| IE (1) | IE40910B1 (en, 2012) |
| LU (2) | LU72249A1 (en, 2012) |
| NL (2) | NL7504368A (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4301306A (en) * | 1980-03-27 | 1981-11-17 | The B. F. Goodrich Company | Norbornenyl phenolic compounds |
| JPS59116242A (ja) * | 1982-12-22 | 1984-07-05 | Kao Corp | シクロヘキサノ−ル誘導体および香料組成物 |
| ATE25513T1 (de) * | 1983-05-24 | 1987-03-15 | Dow Chemical Co | Bis(norbornyl oder substituierte norbornyl)derivate eines phenols oder phenylamines, verfahren zu ihrer herstellung und sie enthaltende zusammenstellungen. |
| US5382713A (en) * | 1993-02-05 | 1995-01-17 | Shell Oil Company | Phenolic compounds |
| RU2406487C1 (ru) * | 2009-05-06 | 2010-12-20 | Учреждение Российской академии медицинских наук Научно-исследовательский институт фармакологии Сибирского отделения РАМН | Средство, обладающее ретинопротекторной активностью |
| CN103250099B (zh) * | 2010-09-28 | 2015-07-22 | 普罗米鲁斯有限责任公司 | 降冰片烷-基pac ballast和包含该pac的正色调光敏树脂组合物 |
| WO2013006098A2 (ru) * | 2011-07-06 | 2013-01-10 | Федеральное Государственное Бюджетное Учреждение Науки Институт Химии Коми Научного Центра Уральского Отделения Российской Академии Наук | Производные 2,6-диизоборнилфенола |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2289550A (en) * | 1940-08-07 | 1942-07-14 | American Cyanamid Co | Nitro bornyl phenols as insecticides |
| US2537647A (en) * | 1948-02-21 | 1951-01-09 | Firestone Tire & Rubber Co | Rearrangement of terpenyl aryl ethers |
| US3878254A (en) * | 1962-11-28 | 1975-04-15 | Marpha Societe A Responsibilit | 6-isoformyl-3,4-xylenol and a process for its preparation |
| FR1355165A (fr) | 1963-04-11 | 1964-03-13 | Wolfen Filmfab Veb | Procédé de préparation de phénols terpéniques et de leurs éthers, et produits obtenus |
| GB1306217A (en, 2012) * | 1969-07-04 | 1973-02-07 |
-
1974
- 1974-04-11 GB GB16142/74A patent/GB1510302A/en not_active Expired
-
1975
- 1975-04-01 FR FR7510168A patent/FR2267093B1/fr not_active Expired
- 1975-04-02 CH CH415475A patent/CH593891A5/xx not_active IP Right Cessation
- 1975-04-02 CH CH415575A patent/CH593221A5/xx not_active IP Right Cessation
- 1975-04-07 IE IE773/75A patent/IE40910B1/xx unknown
- 1975-04-09 LU LU72249A patent/LU72249A1/xx unknown
- 1975-04-09 DE DE19752515382 patent/DE2515382A1/de not_active Withdrawn
- 1975-04-09 US US05/566,364 patent/US4067899A/en not_active Expired - Lifetime
- 1975-04-09 LU LU72250A patent/LU72250A1/xx unknown
- 1975-04-10 BE BE155288A patent/BE827797A/xx not_active IP Right Cessation
- 1975-04-10 DK DK154075AA patent/DK142170B/da not_active IP Right Cessation
- 1975-04-10 DK DK154175AA patent/DK142358B/da not_active IP Right Cessation
- 1975-04-11 CA CA224,571A patent/CA1055529A/en not_active Expired
- 1975-04-11 CA CA224,583A patent/CA1045164A/fr not_active Expired
- 1975-04-11 JP JP50043491A patent/JPS5830289B2/ja not_active Expired
- 1975-04-11 NL NL7504368A patent/NL7504368A/xx not_active Application Discontinuation
- 1975-04-11 NL NL7504369A patent/NL7504369A/xx not_active Application Discontinuation
- 1975-04-11 JP JP50043490A patent/JPS5830288B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH593891A5 (en, 2012) | 1977-12-30 |
| DK142358B (da) | 1980-10-20 |
| CH593221A5 (en, 2012) | 1977-11-30 |
| JPS5830288B2 (ja) | 1983-06-28 |
| JPS51118753A (en) | 1976-10-18 |
| FR2267093A1 (en, 2012) | 1975-11-07 |
| NL7504368A (nl) | 1975-10-14 |
| JPS5830289B2 (ja) | 1983-06-28 |
| DK142358C (en, 2012) | 1981-07-06 |
| DK154075A (en, 2012) | 1975-10-12 |
| IE40910L (en) | 1975-10-11 |
| DK154175A (en, 2012) | 1975-10-12 |
| CA1045164A (fr) | 1978-12-26 |
| IE40910B1 (en) | 1979-09-12 |
| LU72249A1 (en, 2012) | 1975-08-20 |
| NL7504369A (nl) | 1975-10-14 |
| DK142170C (en, 2012) | 1981-02-09 |
| JPS50151857A (en, 2012) | 1975-12-06 |
| US4067899A (en) | 1978-01-10 |
| GB1510302A (en) | 1978-05-10 |
| BE827797A (fr) | 1975-07-31 |
| DK142170B (da) | 1980-09-15 |
| LU72250A1 (en, 2012) | 1975-08-20 |
| DE2515382A1 (de) | 1975-11-06 |
| FR2267093B1 (en, 2012) | 1980-02-22 |
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