BR9916471A - Processo para a sìntese 5-(alfa-hidróxialquil) benzo[1,3 ] dioxóis - Google Patents
Processo para a sìntese 5-(alfa-hidróxialquil) benzo[1,3 ] dioxóisInfo
- Publication number
- BR9916471A BR9916471A BR9916471-0A BR9916471A BR9916471A BR 9916471 A BR9916471 A BR 9916471A BR 9916471 A BR9916471 A BR 9916471A BR 9916471 A BR9916471 A BR 9916471A
- Authority
- BR
- Brazil
- Prior art keywords
- benzo
- hydroxyalkyl
- dioxol
- dioxols
- synthesis
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 6
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical class C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 title abstract 5
- 230000015572 biosynthetic process Effects 0.000 title abstract 5
- 238000003786 synthesis reaction Methods 0.000 title abstract 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 abstract 1
- 239000002917 insecticide Substances 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
-
- 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
- C07D317/54—Radicals substituted by oxygen atoms
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Fats And Perfumes (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Abstract
<B>"PROCESSO PARA A SìNTESE DE 5-(<244>-HIDRóXIALQUIL) BENZO [1,3] DIOXóIS"<D>. A presente invenção se refere a um processo em três etapas, para síntese de 5-(<244>-hidróxialquil) - benzo [1,3] dioxóis. O processo compreende: (i) reação de pirocatequin (1,2-dihidróxibenzeno) com um dihalo ou dialcóxialcano, com a formação de um derivado benzo [1,3] dioxol; (ii) acilação catalítica 5-seletiva do benzo [1,3] dioxol com formação de 5-alcanoilbenzo [1, 3] dioxol e sua subsequente (iii) redução a 5-(<244>-hidróxialquil) benzo [1,3] dioxol. Também descrito na presente invenção são os novos compostos de benzodioxol obtidos através do uso do processo acima mencionado. O processo da invenção é industrialmente simples e apresenta um baixo impacto ambiental; permite a obtenção de derivados de considerável interesse com altos rendimentos, em particular para a indústria de perfumaria e no setor de inseticidas.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT1998MI002857A IT1304513B1 (it) | 1998-12-30 | 1998-12-30 | Processo per la sintesi di 5-(alfa-idrossialchil)benzo(1,3)diossoli. |
PCT/EP1999/007743 WO2000040575A1 (en) | 1998-12-30 | 1999-10-14 | PROCESS FOR THE SYNTHESIS OF 5-(α -HYDROXYALKYL) BENZO[1, 3]DIOXOLS |
Publications (2)
Publication Number | Publication Date |
---|---|
BR9916471A true BR9916471A (pt) | 2001-09-18 |
BR9916471B1 BR9916471B1 (pt) | 2010-12-14 |
Family
ID=11381378
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BRPI9916471-0A BR9916471B1 (pt) | 1998-12-30 | 1999-10-14 | processo para a sÍntese de 5-(alfa-hidràxialquil) benzo [1,3] dioxàis. |
Country Status (13)
Country | Link |
---|---|
US (1) | US6342613B1 (pt) |
EP (1) | EP1140894B1 (pt) |
JP (1) | JP4845266B2 (pt) |
KR (1) | KR100682160B1 (pt) |
CN (1) | CN1138769C (pt) |
AT (1) | ATE256676T1 (pt) |
AU (1) | AU756172B2 (pt) |
BR (1) | BR9916471B1 (pt) |
CA (1) | CA2352249C (pt) |
DE (1) | DE69913735T2 (pt) |
IT (1) | IT1304513B1 (pt) |
RU (1) | RU2243224C2 (pt) |
WO (1) | WO2000040575A1 (pt) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9290473B2 (en) | 2009-01-12 | 2016-03-22 | Coucil Of Scientific & Industrial Research | Inhibitors of phosphatidylinositol-3-kinase (PI3) and inducers of nitric oxide (NO) |
EP2289889A1 (en) | 2009-08-18 | 2011-03-02 | Endura S.p.a. | Substituted alkynyl phenoxy compounds and their uses |
CN102070596B (zh) * | 2011-01-22 | 2013-02-27 | 浙江大学 | 二氢黄樟素的制备方法 |
GB201104156D0 (en) | 2011-03-11 | 2011-04-27 | Rothamstead Res Ltd | Compositions and methods for controlling pesticide resistant pests |
EP3141115A1 (en) | 2015-09-09 | 2017-03-15 | Endura S.p.a. | Substituted methylenedioxybenzyl compounds and their uses as synergists |
ES2686735T3 (es) | 2015-09-09 | 2018-10-19 | Endura S.P.A. | 2,3-dihidrobenzofuranos 5,7-disustituidos y sus usos como sinergistas |
CN106632228B (zh) * | 2016-08-05 | 2019-07-02 | 成都建中香料香精有限公司 | 一种二氢黄樟素的制备方法 |
WO2018150230A1 (en) | 2017-02-14 | 2018-08-23 | Anthea Aromatics Private Limited | A process for preparation of alkenyl and alkyl derivatives of alkylenedioxybenzene |
WO2022161628A1 (en) | 2021-01-29 | 2022-08-04 | Endura S.P.A. | Process for the preparation of 3,4-methylenedioxypropiophenone |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1097270A (en) * | 1965-10-13 | 1968-01-03 | Shell Int Research | Process for the preparation of methylene dioxybenzene, 1,3-benzoxathiole and derivatives thereof |
US3908000A (en) * | 1971-03-19 | 1975-09-23 | Hoffmann La Roche | Propynyl benzyl ethers as insecticidal agents |
CH583677A5 (pt) * | 1972-02-03 | 1977-01-14 | Basf Ag | |
JPS56164178A (en) * | 1980-05-23 | 1981-12-17 | Mitsubishi Chem Ind Ltd | Preparation of 4-hydroxy-1,3-benzodioxole |
EP0095454A3 (de) * | 1982-05-13 | 1985-04-03 | Gerot-Pharmazeutika Gesellschaft m.b.H. | Neue kernsubstituierte Pyrogallol-Derivate |
JP2521739B2 (ja) * | 1987-01-27 | 1996-08-07 | 新日本薬品株式会社 | 肝臓疾患治療剤 |
US5420301A (en) * | 1988-03-18 | 1995-05-30 | Ciba-Geigy Corporation | Process for the preparation of substituted difluorobenzo-1,3-dioxoles |
JP2760998B2 (ja) * | 1988-08-16 | 1998-06-04 | 新日本薬品株式会社 | 肝臓疾患治療剤 |
DE4133155A1 (de) * | 1991-10-07 | 1993-04-08 | Bayer Ag | Verfahren zur herstellung von 2,2-difluorbenzo (1,3)-dioxol-carbaldehyden und neuen zwischenprodukten |
US5696301A (en) * | 1996-01-23 | 1997-12-09 | Ube Industries, Ltd. | Process for preparing protocatechualdehyde |
-
1998
- 1998-12-30 IT IT1998MI002857A patent/IT1304513B1/it active
-
1999
- 1999-10-14 JP JP2000592283A patent/JP4845266B2/ja not_active Expired - Lifetime
- 1999-10-14 BR BRPI9916471-0A patent/BR9916471B1/pt not_active IP Right Cessation
- 1999-10-14 WO PCT/EP1999/007743 patent/WO2000040575A1/en active IP Right Grant
- 1999-10-14 DE DE69913735T patent/DE69913735T2/de not_active Expired - Lifetime
- 1999-10-14 CN CNB998151173A patent/CN1138769C/zh not_active Expired - Lifetime
- 1999-10-14 KR KR1020017007081A patent/KR100682160B1/ko active IP Right Grant
- 1999-10-14 AU AU10377/00A patent/AU756172B2/en not_active Expired
- 1999-10-14 EP EP99953826A patent/EP1140894B1/en not_active Expired - Lifetime
- 1999-10-14 US US09/856,752 patent/US6342613B1/en not_active Expired - Lifetime
- 1999-10-14 RU RU2001117199/04A patent/RU2243224C2/ru active
- 1999-10-14 CA CA002352249A patent/CA2352249C/en not_active Expired - Lifetime
- 1999-10-14 AT AT99953826T patent/ATE256676T1/de not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
JP2002534423A (ja) | 2002-10-15 |
IT1304513B1 (it) | 2001-03-19 |
RU2243224C2 (ru) | 2004-12-27 |
CN1138769C (zh) | 2004-02-18 |
EP1140894A1 (en) | 2001-10-10 |
WO2000040575A1 (en) | 2000-07-13 |
EP1140894B1 (en) | 2003-12-17 |
CA2352249C (en) | 2007-09-11 |
CA2352249A1 (en) | 2000-07-13 |
ITMI982857A0 (it) | 1998-12-30 |
ATE256676T1 (de) | 2004-01-15 |
BR9916471B1 (pt) | 2010-12-14 |
JP4845266B2 (ja) | 2011-12-28 |
DE69913735D1 (de) | 2004-01-29 |
US6342613B1 (en) | 2002-01-29 |
KR100682160B1 (ko) | 2007-02-12 |
ITMI982857A1 (it) | 2000-06-30 |
AU756172B2 (en) | 2003-01-09 |
DE69913735T2 (de) | 2004-07-29 |
KR20010083955A (ko) | 2001-09-03 |
CN1332736A (zh) | 2002-01-23 |
AU1037700A (en) | 2000-07-24 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
B06A | Patent application procedure suspended [chapter 6.1 patent gazette] | ||
B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
B09W | Correction of the decision to grant [chapter 9.1.4 patent gazette] |
Free format text: REFERENTE A RPI 2029 DE 24/11/2009. |
|
B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 10 (DEZ) ANOS CONTADOS A PARTIR DE 14/12/2010, OBSERVADAS AS CONDICOES LEGAIS. |
|
B21A | Patent or certificate of addition expired [chapter 21.1 patent gazette] |
Free format text: PATENTE EXTINTA EM 14.12.2020 |