ES2186605T3 - Procedimiento para la sintesis de 5-alilbenzodioxoles. - Google Patents
Procedimiento para la sintesis de 5-alilbenzodioxoles.Info
- Publication number
- ES2186605T3 ES2186605T3 ES00107834T ES00107834T ES2186605T3 ES 2186605 T3 ES2186605 T3 ES 2186605T3 ES 00107834 T ES00107834 T ES 00107834T ES 00107834 T ES00107834 T ES 00107834T ES 2186605 T3 ES2186605 T3 ES 2186605T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- compound
- give
- alkyl
- synthesis
- 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 - Lifetime
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 7
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical class C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 241000287531 Psittacidae Species 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000007514 bases Chemical class 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000002484 inorganic compounds Chemical class 0.000 abstract 1
- 229910010272 inorganic material Inorganic materials 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fats And Perfumes (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Luminescent Compositions (AREA)
- Light Receiving Elements (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Procedimiento para la síntesis de 5-alquilbenzo[1, 3]dioxoles, consistente en los siguientes pasos: (a) hidrogenación catalítica del 4-acilfenol de fórmula (I), donde R1 es un alquilo C1-C17, para dar 4-alquilfenol de fórmula (II) **(Fórmula)** (b) acilación del compuesto (II) con un grupo acilo que contenga hasta 3 átomos de carbono para dar un compuesto de fórmula (III), donde R3 es metilo o etilo **(Fórmula)** (c) tratamiento del compuesto (III) con un ácido de Lewis para dar 4-alquil-2-acilfenol (IV) **(Fórmula)** (d) tratamiento del compuesto (IV) a de 0°C a 25°C con peróxido de hidrógeno y una solución hidroalcohólica que contenga un compuesto inorgánico básico, en una proporción molar de compuesto básico/compuesto (IV) de 0, 8:1 hasta 2:1 para dar 4-alquilcatecol (V) **(Fórmula)** (e) ciclización del compuesto (V) con un compuesto de fórmula X-CH(R2)-Y, donde X e Y, idénticas o diferentes, se pueden seleccionar cada una: (i) entre el grupo formado por cloro, bromo, yodo, o (ii) entreel grupo formado por CH3O-, C2H5O-, y donde R2 es H, o un alquilo C1-C3, para dar 5-alquilbenzo[1, 3]dioxol (VI). **(Fórmula)**
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1999MI000922A IT1312551B1 (it) | 1999-04-30 | 1999-04-30 | Processo per la sintesi di 5-alchilbenzodiossoli |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2186605T3 true ES2186605T3 (es) | 2003-05-16 |
Family
ID=11382851
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00107834T Expired - Lifetime ES2186605T3 (es) | 1999-04-30 | 2000-04-12 | Procedimiento para la sintesis de 5-alilbenzodioxoles. |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6252092B1 (es) |
| EP (1) | EP1048664B1 (es) |
| JP (1) | JP4707796B2 (es) |
| DE (1) | DE60000759T2 (es) |
| ES (1) | ES2186605T3 (es) |
| IT (1) | IT1312551B1 (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6384247B2 (en) * | 2000-06-19 | 2002-05-07 | Daicel Chemical Industries, Ltd. | Method of producing sesamol formic acid ester and sesamol |
| WO2018150230A1 (en) | 2017-02-14 | 2018-08-23 | Anthea Aromatics Private Limited | A process for preparation of alkenyl and alkyl derivatives of alkylenedioxybenzene |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL251830A (es) * | 1958-12-16 | |||
| GB1097270A (en) * | 1965-10-13 | 1968-01-03 | Shell Int Research | Process for the preparation of methylene dioxybenzene, 1,3-benzoxathiole and derivatives thereof |
| JPS5835193B2 (ja) * | 1974-08-30 | 1983-08-01 | 丸善石油株式会社 | ３．４− メチレンジオキシスチレンノセイゾウホウホウ |
-
1999
- 1999-04-30 IT IT1999MI000922A patent/IT1312551B1/it active
-
2000
- 2000-04-12 DE DE60000759T patent/DE60000759T2/de not_active Expired - Lifetime
- 2000-04-12 EP EP00107834A patent/EP1048664B1/en not_active Expired - Lifetime
- 2000-04-12 ES ES00107834T patent/ES2186605T3/es not_active Expired - Lifetime
- 2000-04-13 US US09/548,763 patent/US6252092B1/en not_active Expired - Lifetime
- 2000-04-20 JP JP2000119522A patent/JP4707796B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IT1312551B1 (it) | 2002-04-22 |
| EP1048664A3 (en) | 2001-03-21 |
| DE60000759D1 (de) | 2002-12-19 |
| ITMI990922A1 (it) | 2000-10-30 |
| EP1048664A2 (en) | 2000-11-02 |
| US6252092B1 (en) | 2001-06-26 |
| EP1048664B1 (en) | 2002-11-13 |
| JP4707796B2 (ja) | 2011-06-22 |
| JP2000336086A (ja) | 2000-12-05 |
| DE60000759T2 (de) | 2003-08-14 |
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