FR2453843A1 - Antibacterial 6-iso-bornyl-3,4-xylenol prepn. - by condensing camphene with 6-iso-bornyl-3,4-xylenol-benzyl ether (sic) using Friedel-Crafts catalyst, hydrogenating and de:benzylating - Google Patents
Antibacterial 6-iso-bornyl-3,4-xylenol prepn. - by condensing camphene with 6-iso-bornyl-3,4-xylenol-benzyl ether (sic) using Friedel-Crafts catalyst, hydrogenating and de:benzylatingInfo
- Publication number
- FR2453843A1 FR2453843A1 FR7909137A FR7909137A FR2453843A1 FR 2453843 A1 FR2453843 A1 FR 2453843A1 FR 7909137 A FR7909137 A FR 7909137A FR 7909137 A FR7909137 A FR 7909137A FR 2453843 A1 FR2453843 A1 FR 2453843A1
- Authority
- FR
- France
- Prior art keywords
- xylenol
- bornyl
- iso
- hydrogenating
- camphene
- 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.)
- Pending
Links
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 title abstract 4
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 title abstract 2
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 title abstract 2
- 229930006739 camphene Natural products 0.000 title abstract 2
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 title abstract 2
- 239000003054 catalyst Substances 0.000 title abstract 2
- RNRHMQWZFJXKLZ-XUWXXGDYSA-N xibornol Chemical compound C1=C(C)C(C)=CC(O)=C1[C@H]1[C@](C2(C)C)(C)CC[C@@H]2C1 RNRHMQWZFJXKLZ-XUWXXGDYSA-N 0.000 title abstract 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 title 1
- 230000000844 anti-bacterial effect Effects 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 238000006264 debenzylation reaction Methods 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
Classifications
-
- 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
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
-
- 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
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Prodn. of 6-isobornyl-3,4-xylenol of formula (I) comprises reacting camphene with 6-isobornyl-3,4-xylenol-benzyl, ether at about 0 degrees C in an organic solvent (e.g. ethyl, ether, benzene or nitrobenzene) in the presence of Friedel Crafts (e.g. AlCl3) by condensn.; and hydrogenating the prod. and a debenzylation in the presence of hydrogenating catalyst. (I) is a strong antibacterial agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7909137A FR2453843A1 (en) | 1979-04-11 | 1979-04-11 | Antibacterial 6-iso-bornyl-3,4-xylenol prepn. - by condensing camphene with 6-iso-bornyl-3,4-xylenol-benzyl ether (sic) using Friedel-Crafts catalyst, hydrogenating and de:benzylating |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7909137A FR2453843A1 (en) | 1979-04-11 | 1979-04-11 | Antibacterial 6-iso-bornyl-3,4-xylenol prepn. - by condensing camphene with 6-iso-bornyl-3,4-xylenol-benzyl ether (sic) using Friedel-Crafts catalyst, hydrogenating and de:benzylating |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2453843A1 true FR2453843A1 (en) | 1980-11-07 |
Family
ID=9224207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7909137A Pending FR2453843A1 (en) | 1979-04-11 | 1979-04-11 | Antibacterial 6-iso-bornyl-3,4-xylenol prepn. - by condensing camphene with 6-iso-bornyl-3,4-xylenol-benzyl ether (sic) using Friedel-Crafts catalyst, hydrogenating and de:benzylating |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2453843A1 (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2032170A1 (en) * | 1969-07-04 | 1971-01-14 | Societe dEtudes et dExploitation de Marques MAR PHA, Paris | Process for the production of isobornylphenols |
| FR2402640A1 (en) * | 1977-09-13 | 1979-04-06 | Pfizer | NEW HYDROXYALKYL OR OXOALKYL SUBSTITUTE PHENOLS AND PHARMACEUTICAL COMPOSITION CONTAINING THEM |
-
1979
- 1979-04-11 FR FR7909137A patent/FR2453843A1/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2032170A1 (en) * | 1969-07-04 | 1971-01-14 | Societe dEtudes et dExploitation de Marques MAR PHA, Paris | Process for the production of isobornylphenols |
| FR2402640A1 (en) * | 1977-09-13 | 1979-04-06 | Pfizer | NEW HYDROXYALKYL OR OXOALKYL SUBSTITUTE PHENOLS AND PHARMACEUTICAL COMPOSITION CONTAINING THEM |
Non-Patent Citations (1)
| Title |
|---|
| CA1979 * |
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