IL24061A - Process for the preparation of substituted gamma-lactones and products resulting from this process - Google Patents

Process for the preparation of substituted gamma-lactones and products resulting from this process

Info

Publication number: IL24061A
Authority: IL; Israel
Prior art keywords: phenyl; hydrogen; group; alkyl; preparation
Prior art date: 1964-08-06

Application number

IL24061A

Other languages

English (en)

Original Assignee

Roussel Uclaf

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.)

1964-08-06

Filing date

1965-07-29

Publication date

1970-06-17

1965-07-29 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1970-06-17 Publication of IL24061A publication Critical patent/IL24061A/en

Links

238000000034 method Methods 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title claims description 6
125000000457 gamma-lactone group Chemical group 0.000 title description 2
-1 lower-alkyl-phenyl Chemical group 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
150000002431 hydrogen Chemical class 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000005059 halophenyl group Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
238000010992 reflux Methods 0.000 claims description 5
239000012736 aqueous medium Substances 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
239000000908 ammonium hydroxide Substances 0.000 claims description 2
150000002596 lactones Chemical class 0.000 description 8
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
150000003457 sulfones Chemical class 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000000203 mixture Substances 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
229920002554 vinyl polymer Polymers 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
QXAOXNGMVGUIRO-UHFFFAOYSA-N 4-hydroxy-3,3,6-trimethylhept-5-enoic acid Chemical compound CC(CC(=O)O)(C(C=C(C)C)O)C QXAOXNGMVGUIRO-UHFFFAOYSA-N 0.000 description 1
BYNRIZXXWYZZGC-UHFFFAOYSA-N 4-hydroxy-6-methyl-3-phenylhept-5-enoic acid Chemical compound C1(=CC=CC=C1)C(CC(=O)O)C(C=C(C)C)O BYNRIZXXWYZZGC-UHFFFAOYSA-N 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
241000796533 Arna Species 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000010586 diagram Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
BCYXFRMDZWKZSF-UHFFFAOYSA-N hept-3-enoic acid Chemical compound CCCC=CCC(O)=O BCYXFRMDZWKZSF-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
238000001665 trituration Methods 0.000 description 1
ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 1
239000003643 water by type Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00

Landscapes

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

IL24061A 1964-08-06 1965-07-29 Process for the preparation of substituted gamma-lactones and products resulting from this process IL24061A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR984411A FR1512331A (fr)	1964-08-06	1964-08-06	Procédé de préparation de gamma-lactones substituées et produits en résultant

Publications (1)

Publication Number	Publication Date
IL24061A true IL24061A (en)	1970-06-17

Family

ID=8836239

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL24061A IL24061A (en)	1964-08-06	1965-07-29	Process for the preparation of substituted gamma-lactones and products resulting from this process

Country Status (8)

Country	Link
US (1)	US3320285A (fr)
BE (1)	BE667992A (fr)
CH (1)	CH440247A (fr)
DE (1)	DE1468928A1 (fr)
FR (1)	FR1512331A (fr)
GB (1)	GB1111543A (fr)
IL (1)	IL24061A (fr)
NL (1)	NL139968B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3231815A1 (de) *	1982-08-26	1984-03-01	Bayer Ag, 5090 Leverkusen	Dialkoxymethyl-butyrolactone, verfahren zu ihrer herstellung, zwischenprodukte dafuer und ihre verwendung
US4954623A (en) *	1989-03-20	1990-09-04	Eli Lilly And Company	Recovery of difluoro sugar

1964
- 1964-08-06 FR FR984411A patent/FR1512331A/fr not_active Expired
1965
- 1965-07-28 CH CH1060165A patent/CH440247A/fr unknown
- 1965-07-29 IL IL24061A patent/IL24061A/en unknown
- 1965-08-03 US US477013A patent/US3320285A/en not_active Expired - Lifetime
- 1965-08-05 GB GB33627/65A patent/GB1111543A/en not_active Expired
- 1965-08-06 DE DE19651468928 patent/DE1468928A1/de active Pending
- 1965-08-06 NL NL656510242A patent/NL139968B/xx not_active IP Right Cessation
- 1965-08-06 BE BE667992D patent/BE667992A/xx unknown

Also Published As

Publication number	Publication date
DE1468928A1 (de)	1969-04-17
FR1512331A (fr)	1968-02-09
BE667992A (fr)	1966-02-07
GB1111543A (en)	1968-05-01
NL6510242A (fr)	1966-02-07
US3320285A (en)	1967-05-16
CH440247A (fr)	1967-07-31
NL139968B (nl)	1973-10-15

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US3739019A (en)	1973-06-12	Preparation of optically active trans chrysanthemic acid
IL24061A (en)	1970-06-17	Process for the preparation of substituted gamma-lactones and products resulting from this process
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JPS5210214A (en)	1977-01-26	Process for recovery of methylmethacrylate dimer
Geissman et al.	1941	The Reaction between Cyclic β-Diketones and Grignard Reagents. 1, 3-Diketo-2, 2-dimethylhydrindene1
IL28401A (en)	1971-04-28	Arylsulfonyl ureas,their manufacture and pharmaceutical compositions containing them
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JPS5430128A (en)	1979-03-06	Preparation of water impregnated substance of diperisophthalic acid tent-butyl ester
SU170492A1 (ru)	1965-04-23	Способ получени хлорангидридов N-ациларениминосульфиновых кислот
GB1389104A (en)	1975-04-03	Process for preparing beta, delta-dioxoenanthaldehyde dialkyl acetals
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DE1793175A1 (de)	1972-03-30	Verfahren zur Herstellung von Furansaeure-Derivaten
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