NO171106B - PROCEDURE FOR THE PREPARATION OF 2-BENZYL-1-NAFTHOL - Google Patents
PROCEDURE FOR THE PREPARATION OF 2-BENZYL-1-NAFTHOL Download PDFInfo
- Publication number
- NO171106B NO171106B NO900651A NO900651A NO171106B NO 171106 B NO171106 B NO 171106B NO 900651 A NO900651 A NO 900651A NO 900651 A NO900651 A NO 900651A NO 171106 B NO171106 B NO 171106B
- Authority
- NO
- Norway
- Prior art keywords
- benzyl
- tetralone
- naphthol
- mol
- benzaldehyde
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title abstract description 4
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 claims abstract description 12
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 12
- CZTSOXCSVFEFIK-UHFFFAOYSA-N 2-benzylnaphthalen-1-ol Chemical compound C1=CC2=CC=CC=C2C(O)=C1CC1=CC=CC=C1 CZTSOXCSVFEFIK-UHFFFAOYSA-N 0.000 claims abstract description 10
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims abstract description 10
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- RCTSPIJCLVGXIM-UHFFFAOYSA-N 2-[(2-hydroxyphenyl)methyl]naphthalen-1-ol Chemical compound OC1=CC=CC=C1CC1=CC=C(C=CC=C2)C2=C1O RCTSPIJCLVGXIM-UHFFFAOYSA-N 0.000 claims description 2
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JNRAEZULKWNOQO-UHFFFAOYSA-N 2-benzylidene-3,4-dihydronaphthalen-1-one Chemical compound C1CC2=CC=CC=C2C(=O)C1=CC1=CC=CC=C1 JNRAEZULKWNOQO-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- RZPFVRFSYMUDJO-UHFFFAOYSA-N 2h-naphthalen-1-one Chemical class C1=CC=C2C(=O)CC=CC2=C1 RZPFVRFSYMUDJO-UHFFFAOYSA-N 0.000 description 1
- 241001143131 Ononis natrix Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Foreliggende oppfinnelse angår en ny fremgangsmåte for fremstilling av 2-benzyl-l-nafthol av formel. Ved fremgangsmåten ifølge foreliggende oppfinnelse behandles en blanding av benzaldehyd og alfa-tetralon i t-butanol med kalium-t-butoxyd.The present invention relates to a novel process for the preparation of 2-benzyl-1-naphthol of formula. In the process of the present invention, a mixture of benzaldehyde and alpha-tetralone in t-butanol is treated with potassium t-butoxide.
Description
Foreliggende oppfinnelse angår en fremgangsmåte for fremstilling av 2-benzyl-l-nafthol. The present invention relates to a method for the production of 2-benzyl-1-naphthol.
Kjent teknikk Known technique
Et utall publikasjoner beskriver 2-alkyl-l-naftholer som mellomprodukter ved fremstilling av andre kjemiske for-bindelser, innbefattende N.S. Narasimhan og R.S. Mali, Tetrahedron, 31, 1005 (1975); Newman et al., J. Org. Chem., 43, 524 (1978); B. Miller og W. Lin, J. Org. Chem., .43, 4441 A number of publications describe 2-alkyl-1-naphthols as intermediates in the preparation of other chemical compounds, including N.S. Narasimhan and R.S. Mali, Tetrahedron, 31, 1005 (1975); Newman et al., J. Org. Chem., 43, 524 (1978); B. Miller and W. Lin, J. Org. Chem., .43, 4441
(1978); K.A. Parker og J.L. Kallmerton, Tetrahedron Letters, 14, 1197 (1979); D.W. Cameron et al., Aust J. Chem, 35, 1481 (1978); K. A. Parker and J.L. Kallmerton, Tetrahedron Letters, 14, 1197 (1979); D.W. Cameron et al., Aust J. Chem, 35, 1481
(1982); P. Barua et al., Chem. Ind., 303, (1984); T. (1982); P. Barua et al., Chem. Ind., 303, (1984); T.
Kometani et al., J. Org. Chem., 48, 2630 (1983); T. Zhong og M. Huang, Hua Hseuh Hseuh Pao, 39, 229 (1981); C. Pac et Kometani et al., J. Org. Chem., 48, 2630 (1983); T. Zhong and M. Huang, Hua Hseuh Hseuh Pao, 39, 229 (1981); C. Pac et
al., Synthesis, 589 (1978); I.A. Akhtar og J.J. McCullough i J. Org. Chem., 4_6, 1447 (1981); R. Alonso Cermona et al., al., Synthesis, 589 (1978); I.A. Akhtar and J.J. McCullough in J. Org. Chem., 4-6, 1447 (1981); R. Alonso Cermona et al.,
An. Quim., Ser. C., 78, 9 (1982); I.M. Andreeva et al., An. Quim., Ser. C., 78, 9 (1982); I. M. Andreeva et al.,
Khim. Geterotsikl. Soedin., 2, 181 (1983); D. Berney og Kr Schuh, Heiv. Chim. Acta, 62, 1268 (1979); S.P. Starkov, Izv. Vyssh. Uchebn. Zaved., Khim. Khim Tekhnol., 20, 1099 (1977); M.R. Saidi, Indian J. Chem., 474 (1982); L.Z. Oblasova og G.D. Kharlampovich, Khim. Pro-St. (Moscow), 10, 776 (1977); F.T. Sher og G.A. Berchtold, J. Org. Chem., 42, 2569 (1977); M. Mully et al., Heiv. Chim. Acta, 58, 610 (1975); T.R. Kasturi og R. Sivaramakrishnan, Proe. Indian Acad. Sei., 86, 309 (1977) og T. Hirashima et al. i japansk patent nr. 7010339, bevilget 14. april 1970. Kim. Goat root cycle. Soedin., 2, 181 (1983); D. Berney and Kr Schuh, Heiv. Chim. Acta, 62, 1268 (1979); S. P. Starkov, Izv. Vyssh. Uchebn. Zaved., Khim. Khim Technol., 20, 1099 (1977); M. R. Saidi, Indian J. Chem., 474 (1982); L.Z. Oblasova and G.D. Kharlampovich, Khim. Pro-St. (Moscow), 10, 776 (1977); F.T. Sher and G.A. Berchtold, J. Org. Chem., 42, 2569 (1977); M. Mully et al., Heiv. Chim. Acta, 58, 610 (1975); T.R. Kasturi and R. Sivaramakrishnan, Proe. Indian Acad. Sci., 86, 309 (1977) and T. Hirashima et al. in Japanese Patent No. 7010339, granted April 14, 1970.
Et utall publikasjoner beskriver 2-benzyl-l-nafthol A number of publications describe 2-benzyl-1-naphthol
som en kjemisk gruppe, slik som B. Miller og W. Lin, J. Org. Chem., 44, 887 (1979) og Z. Aizenshtat et al., J. Org. as a chemical group, such as B. Miller and W. Lin, J. Org. Chem., 44, 887 (1979) and Z. Aizenshtat et al., J. Org.
Chem., 42, 2386 (1977). Chem., 42, 2386 (1977).
Ifølge oppfinnelsen er det tilveiebrakt en fremgangsmåte for fremstilling av 2-benzyl-l-nafthol av formel: According to the invention, a method has been provided for the production of 2-benzyl-1-naphthol of the formula:
hvori det som utgangsmateriale anvendes tetralon og benzaldehyd, kjennetegnet ved at en blanding av benzaldehyd og alfa-tetralon i t-butanol behandles med kaliumbutoxyd. in which tetralone and benzaldehyde are used as starting materials, characterized in that a mixture of benzaldehyde and alpha-tetralone in t-butanol is treated with potassium butoxide.
Fremgangsmåten ifølge den ovenfor refererte publikasjon av Miller et al. beskriver en omleiring av nafthalenoner i syre. Alt denne synes å gjøre er å forskyve carbonylgruppen eller frembringe en ny carbonylgruppe som kan derivatiseres videre. The method according to the above-referenced publication by Miller et al. describes a rearrangement of naphthalenones in acid. All this seems to do is displace the carbonyl group or produce a new carbonyl group which can be derivatized further.
Den refererte publikasjon av Aizenshtat et al. angir i første avsnitt at de nå eksisterende (1976) synteser er fremgangsmåter som er ineffektive og som gir lave utbytter. På side 2388 beskriver Aizenshtat fremstilling av 2-benzyl-l-naf thol ved isoaromatisering, som vist i 8-10 og i figur 2. Som det fremgår er katalysatorsystemet og løsningsmiddel systemet temmelig kompleks og, som vist under figur 2, har difenylether et kokepunkt ved 255 °C. The referenced publication by Aizenshtat et al. states in the first paragraph that the now existing (1976) syntheses are procedures which are inefficient and which give low yields. On page 2388, Aizenshtat describes the preparation of 2-benzyl-l-naphthol by isoaromatization, as shown in 8-10 and in figure 2. As can be seen, the catalyst system and solvent system are rather complex and, as shown under figure 2, diphenyl ether has a boiling point at 255 °C.
Fremgangsmåten ifølge foreliggende oppfinnelse anvender i forhold enkle reaksjonsmediematerialer, mindre strenge betingelser og starter direkte med tetralon og benzaldehyd uten å gå via benzylidén. The method according to the present invention uses relatively simple reaction medium materials, less stringent conditions and starts directly with tetralone and benzaldehyde without going via the benzylidene.
Den angitte referanse av Barton et al. viser på s. 16 i beskrivelsen at 2-benzyl-l-nafthol fremstilles ved isomeri-sering av et benzyliden-tetralon med en rhodium-katalysator i etanolkloroform. The cited reference by Barton et al. shows on p. 16 of the description that 2-benzyl-1-naphthol is produced by isomerization of a benzylidene tetralone with a rhodium catalyst in ethanol chloroform.
Kjent teknikk viser ved disse referanser en reaksjonsrekke som går fra tetralon til en intermediær forbindelse og deretter til 2-benzyl-l-nafthol. Fremgangsmåten ifølge foreliggende oppfinnelse går fra et tetralon direkte til 2-benzyl-l-nafthol uten å gå gjennom en særskilt intermediær forbindelse, ved at reaksjonen utføres i t-butanol med t-butoxyd. Dette er nytt; det sparer et fremgangsmåtetrinn og anvender enkle materialer og ikke fremmedartede katalysatorer som anvendt i fremgangsmåten ifølge de refererte publikasjoner . Known technology shows in these references a reaction series that goes from tetralone to an intermediate compound and then to 2-benzyl-1-naphthol. The method according to the present invention goes from a tetralone directly to 2-benzyl-1-naphthol without going through a special intermediate compound, by the reaction being carried out in t-butanol with t-butoxide. This is new; it saves a method step and uses simple materials and not foreign catalysts as used in the method according to the referenced publications.
Ved anvendelse av fremgangsmåten ifølge foreliggende oppfinnelse fremstilles 2-benzyl-l-nafthol analogt med det nedenfor beskrevne utførelseseksempel for fremstilling av 2-(2-hydroxyfenylmethyl)-l-nafthol. When using the method according to the present invention, 2-benzyl-1-naphthol is produced analogously to the embodiment described below for the production of 2-(2-hydroxyphenylmethyl)-1-naphthol.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO900651A NO171106C (en) | 1985-05-08 | 1990-02-09 | PROCEDURE FOR THE PREPARATION OF 2-BENZYL-1-NAFTHOL |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73179185A | 1985-05-08 | 1985-05-08 | |
| US06/839,912 US4833164A (en) | 1985-05-08 | 1986-03-19 | 2-substituted-1-naphthols, pharmaceutical compositions of, and their use as 5-lipoxygenase inhibitors |
| NO861829A NO164592C (en) | 1985-05-08 | 1986-05-07 | PROCEDURE FOR THE PREPARATION OF 2-SUBSTITUTED-1-NAFTHOLS. |
| NO900651A NO171106C (en) | 1985-05-08 | 1990-02-09 | PROCEDURE FOR THE PREPARATION OF 2-BENZYL-1-NAFTHOL |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO900651L NO900651L (en) | 1986-11-10 |
| NO900651D0 NO900651D0 (en) | 1990-02-09 |
| NO171106B true NO171106B (en) | 1992-10-19 |
| NO171106C NO171106C (en) | 1993-01-27 |
Family
ID=27484135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO900651A NO171106C (en) | 1985-05-08 | 1990-02-09 | PROCEDURE FOR THE PREPARATION OF 2-BENZYL-1-NAFTHOL |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO171106C (en) |
-
1990
- 1990-02-09 NO NO900651A patent/NO171106C/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO900651D0 (en) | 1990-02-09 |
| NO171106C (en) | 1993-01-27 |
| NO900651L (en) | 1986-11-10 |
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