CA1110255A - Method for the preparation of 2,5-dialkyl-4-hydroxy-2, 3-dihydrofuran-3-ones - Google Patents

Method for the preparation of 2,5-dialkyl-4-hydroxy-2, 3-dihydrofuran-3-ones

Info

Publication number: CA1110255A
Authority: CA; Canada
Prior art keywords: dihydrofuran; hydroxy; preparation; dialkyl; ones
Prior art date: 1977-10-20
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

Application number

CA312,375A

Other languages

English (en)

French (fr)

Inventor

Valerio Caciagli

Giancarlo Eletti Bianchi

Bruno Biancini

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.)

SnamProgetti SpA

Original Assignee

SnamProgetti 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.)

1977-10-20

Filing date

1978-09-29

Publication date

1981-10-06

1978-09-29 Application filed by SnamProgetti SpA filed Critical SnamProgetti SpA

1981-10-06 Application granted granted Critical

1981-10-06 Publication of CA1110255A publication Critical patent/CA1110255A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 15
238000002360 preparation method Methods 0.000 title claims abstract description 8
239000003729 cation exchange resin Substances 0.000 claims abstract description 3
238000007363 ring formation reaction Methods 0.000 claims description 5
-1 methyl radicals Chemical class 0.000 claims description 4
239000012298 atmosphere Substances 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 3
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 3
239000012429 reaction media Substances 0.000 claims description 3
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
150000003254 radicals Chemical class 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims 1
229940023913 cation exchange resins Drugs 0.000 claims 1
125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims 1
239000011541 reaction mixture Substances 0.000 abstract description 3
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract description 2
238000010992 reflux Methods 0.000 abstract 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
229920005989 resin Polymers 0.000 description 5
239000011347 resin Substances 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
239000002904 solvent Substances 0.000 description 5
INAXVXBDKKUCGI-UHFFFAOYSA-N 4-hydroxy-2,5-dimethylfuran-3-one Chemical compound CC1OC(C)=C(O)C1=O INAXVXBDKKUCGI-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 3
229950005499 carbon tetrachloride Drugs 0.000 description 3
229920001429 chelating resin Polymers 0.000 description 3
QJYOEDXNPLUUAR-UHFFFAOYSA-N 5-ethyl-4-hydroxy-2-methylfuran-3-one Chemical compound CCC1=C(O)C(=O)C(C)O1 QJYOEDXNPLUUAR-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
150000002240 furans Chemical class 0.000 description 2
CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 2
238000002955 isolation Methods 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
238000000746 purification Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OGWRZRITEAGNCV-UHFFFAOYSA-N 2,5-dihydroxyheptane-3,4-dione Chemical compound CCC(O)C(=O)C(=O)C(C)O OGWRZRITEAGNCV-UHFFFAOYSA-N 0.000 description 1
MLOYTUCDJQWVSY-UHFFFAOYSA-N 2,5-dihydroxyhexane-3,4-dione Chemical compound CC(O)C(=O)C(=O)C(C)O MLOYTUCDJQWVSY-UHFFFAOYSA-N 0.000 description 1
GWCRPYGYVRXVLI-UHFFFAOYSA-N 2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone Chemical compound CCC1OC(C)=C(O)C1=O GWCRPYGYVRXVLI-UHFFFAOYSA-N 0.000 description 1
VJMSGSIUSDPZPA-UHFFFAOYSA-N 2-ethyl-5-methylfuran-3-one Chemical compound CCC1OC(C)=CC1=O VJMSGSIUSDPZPA-UHFFFAOYSA-N 0.000 description 1
RYVVJXGADODIJD-UHFFFAOYSA-N 2-hydroxyfuran-3-one Chemical compound OC1OC=CC1=O RYVVJXGADODIJD-UHFFFAOYSA-N 0.000 description 1
SKJNEYSTLJSDDX-UHFFFAOYSA-N 5-ethyl-2-methylfuran-3-one Chemical compound CCC1=CC(=O)C(C)O1 SKJNEYSTLJSDDX-UHFFFAOYSA-N 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
KXUSQYGLNZFMTE-UHFFFAOYSA-N hex-2-yne-1,1-diol Chemical compound CCCC#CC(O)O KXUSQYGLNZFMTE-UHFFFAOYSA-N 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000002304 perfume Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Fats And Perfumes (AREA)
Seasonings (AREA)
Furan Compounds (AREA)
Cosmetics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

CA312,375A 1977-10-20 1978-09-29 Method for the preparation of 2,5-dialkyl-4-hydroxy-2, 3-dihydrofuran-3-ones Expired CA1110255A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT28800A/77		1977-10-20
IT2880077A IT1087026B (it)	1977-10-20	1977-10-20	Procedimento per la preparazione di 2,5-dialchil-4-idrossi-2,3-diidrofuran-3-oni

Publications (1)

Publication Number	Publication Date
CA1110255A true CA1110255A (en)	1981-10-06

Family

ID=11224207

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA312,375A Expired CA1110255A (en)	1977-10-20	1978-09-29	Method for the preparation of 2,5-dialkyl-4-hydroxy-2, 3-dihydrofuran-3-ones

Country Status (10)

Country	Link
JP (1)	JPS5463068A (it)
BE (1)	BE871421A (it)
CA (1)	CA1110255A (it)
CH (1)	CH636611A5 (it)
DE (1)	DE2845843C3 (it)
FR (1)	FR2406636A1 (it)
GB (1)	GB2006205B (it)
IT (1)	IT1087026B (it)
LU (1)	LU80371A1 (it)
NL (1)	NL7810532A (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2831676A1 (de) *	1978-07-19	1980-02-07	Basf Ag	Neue bis-epoxy-dialkoxy-alkane, deren herstellung und verwendung

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1383492A (en) *	1970-12-21	1974-02-12	Unilever Ltd	Dicarbonyl compounds and preparation of dihydrofuranones therefrom

1977
- 1977-10-20 IT IT2880077A patent/IT1087026B/it active
1978
- 1978-09-29 CA CA312,375A patent/CA1110255A/en not_active Expired
- 1978-10-11 GB GB7840115A patent/GB2006205B/en not_active Expired
- 1978-10-16 LU LU80371A patent/LU80371A1/xx unknown
- 1978-10-17 FR FR7829553A patent/FR2406636A1/fr active Granted
- 1978-10-18 JP JP12745678A patent/JPS5463068A/ja active Pending
- 1978-10-19 CH CH1083578A patent/CH636611A5/it not_active IP Right Cessation
- 1978-10-20 NL NL7810532A patent/NL7810532A/xx not_active Application Discontinuation
- 1978-10-20 BE BE191250A patent/BE871421A/xx not_active IP Right Cessation
- 1978-10-20 DE DE19782845843 patent/DE2845843C3/de not_active Expired

Also Published As

Publication number	Publication date
FR2406636B1 (it)	1981-08-14
FR2406636A1 (fr)	1979-05-18
DE2845843B2 (de)	1980-04-30
IT1087026B (it)	1985-05-31
DE2845843A1 (de)	1979-04-26
JPS5463068A (en)	1979-05-21
GB2006205B (en)	1982-03-31
GB2006205A (en)	1979-05-02
BE871421A (fr)	1979-04-20
CH636611A5 (it)	1983-06-15
DE2845843C3 (de)	1980-12-18
LU80371A1 (fr)	1979-03-19
NL7810532A (nl)	1979-04-24

Legal Events

Date	Code	Title	Description
1998-10-06	MKEX	Expiry

Publication	Publication Date	Title
JPS6139949B2 (it)	1986-09-06
KR100346672B1 (ko)	2002-11-23	3-o-치환 아스코르브산의 제조방법
Hoffmann et al.	1989	Chiral induction in photochemical reactions-XII. Synthesis of chiral cyclobutane derivatives from (+)-5-menthyloxy-2-[5H]-furanone and ethylene
CA1110255A (en)	1981-10-06	Method for the preparation of 2,5-dialkyl-4-hydroxy-2, 3-dihydrofuran-3-ones
JPH0826027B2 (ja)	1996-03-13	ギンコライド誘導体およびそれらの調製法
JPH0246590B2 (it)	1990-10-16
JPH0390060A (ja)	1991-04-16	クラウセンアミドおよびネオクラウセンアミド並びにそれらの誘導体の製法
DE2461307C3 (de)	1980-10-30	2-Hydroxymethy!-3-hydroxypyridin-6-epoxyäthan-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von 2-Hydroxymethyl-3hydroxy-6-( 1 -hydrOxy-2-tert.butylaminoäthyDpyridin
JPS5899473A (ja)	1983-06-13	α−アセチルラクトン類の製造方法
Dmowski	1982	Synthesis and intramolecular cyclisation of ortho-hydroxy-2, 3, 3, 3-tetrafluoropropiophenone. Formation of 3-fluoro-4-hydroxycoumarin
KR950005737B1 (ko)	1995-05-30	징코라이드 혼합물로부터 단성분의 분리방법
JPS63258474A (ja)	1988-10-25	カルバゾ−ル、ジベンゾフラン又はジベンゾチオフェン基を含む化合物の水酸基誘導体を調製するための方法
JPH03181459A (ja)	1991-08-07	軟体動物駆除剤の２，４，５―トリブロモピロール―３―カーボニトリル化合物の製造法
JP2622747B2 (ja)	1997-06-18	シス―７―デセン―４―オリドの製造方法
SU1049487A1 (ru)	1983-10-23	Способ получени @ -аминокетонов бензимидазольного р да
SU950724A1 (ru)	1982-08-15	Способ получени третичных дифурилалкил- или фурилфенилкарбинолов
JP4100007B2 (ja)	2008-06-11	シクロペンテノロン類の精製方法
SU1004373A1 (ru)	1983-03-15	Способ получени 3-(1-адамантоил)-5-ароилпиразолин-4-онов
JPS63501949A (ja)	1988-08-04	７α−アセチルチオステロイドの製法
JP2736916B2 (ja)	1998-04-08	シベトンの製造法
JP2787468B2 (ja)	1998-08-20	シス―７―デセン―４―オリドの製法
JPS61210080A (ja)	1986-09-18	アルデヒドラクトンの製造法
Rodios	1985	Fused v-triazolo-heterocycles. Synthesis of 4 hv-triazolo [1, 5-d][1, 3, 4] oxadiatines
JPH0753704B2 (ja)	1995-06-07	フェニルマロン酸モノアニリド誘導体および３―フェニル―２―キノロン誘導体の製造方法
JPS6247171B2 (it)	1987-10-06