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
Application number
ES00107834T
Other languages
English (en)
Inventor
Valerio Borzatta
Dario Brancaleoni
Christian Battistini
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Endura SpA
Original Assignee
Endura SpA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Endura SpA filed Critical Endura SpA
Application granted granted Critical
Publication of ES2186605T3 publication Critical patent/ES2186605T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Luminescent Compositions (AREA)
  • Light Receiving Elements (AREA)
  • Crystals, And After-Treatments Of Crystals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (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)**
ES00107834T 1999-04-30 2000-04-12 Procedimiento para la sintesis de 5-alilbenzodioxoles. Expired - Lifetime ES2186605T3 (es)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE585680A (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

Also Published As

Publication number Publication date
IT1312551B1 (it) 2002-04-22
JP4707796B2 (ja) 2011-06-22
US6252092B1 (en) 2001-06-26
DE60000759D1 (de) 2002-12-19
EP1048664A2 (en) 2000-11-02
JP2000336086A (ja) 2000-12-05
EP1048664B1 (en) 2002-11-13
EP1048664A3 (en) 2001-03-21
ITMI990922A1 (it) 2000-10-30
DE60000759T2 (de) 2003-08-14

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