DD202139A5 - Verfahren zur herstellung von dimedon - Google Patents

Verfahren zur herstellung von dimedon Download PDF

Info

Publication number: DD202139A5
Authority: DD; German Democratic Republic
Prior art keywords: dimethyl; oxo; item; hexanoic acid; dimedone
Prior art date: 1981-05-21

Application number

DD82239906A

Other languages

German (de)

English (en)

Inventor

Pavel Lehky

Peter Kronig

Original Assignee

Lonza Ag

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.)

1981-05-21

Filing date

1982-05-17

Publication date

1983-08-31

1982-05-17 Application filed by Lonza Ag filed Critical Lonza Ag

1983-08-31 Publication of DD202139A5 publication Critical patent/DD202139A5/de

Links

BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical compound CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 title claims abstract description 19
238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 4
SLBXWQKHHZUDAY-UHFFFAOYSA-N 3,3-dimethyl-5-oxohexanoic acid Chemical compound CC(=O)CC(C)(C)CC(O)=O SLBXWQKHHZUDAY-UHFFFAOYSA-N 0.000 claims abstract description 16
230000018044 dehydration Effects 0.000 claims abstract description 12
238000006297 dehydration reaction Methods 0.000 claims abstract description 12
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims abstract description 12
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
230000007062 hydrolysis Effects 0.000 claims abstract description 4
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 11
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 8
ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims description 7
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
238000010533 azeotropic distillation Methods 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 2
-1 alkali metal alkoxide Chemical class 0.000 abstract description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
150000002596 lactones Chemical class 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
XNIHZNNZJHYHLC-UHFFFAOYSA-N 2-oxohexanoic acid Chemical compound CCCCC(=O)C(O)=O XNIHZNNZJHYHLC-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
GUHILFBUKAVJSQ-UHFFFAOYSA-N 4,4-dimethylhexan-2-one Chemical compound CCC(C)(C)CC(C)=O GUHILFBUKAVJSQ-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241001082207 Lactoris Species 0.000 description 1
UOGBWVLAMKCFBK-UHFFFAOYSA-N acetyl acetate;hydrate Chemical compound O.CC(=O)OC(C)=O UOGBWVLAMKCFBK-UHFFFAOYSA-N 0.000 description 1
238000007171 acid catalysis Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000002051 biphasic effect Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
239000010805 inorganic waste Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000003918 potentiometric titration Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/34—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with ozone; by hydrolysis of ozonides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DD82239906A 1981-05-21 1982-05-17 Verfahren zur herstellung von dimedon DD202139A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH332181		1981-05-21

Publications (1)

Publication Number	Publication Date
DD202139A5 true DD202139A5 (de)	1983-08-31

Family

ID=4253454

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD82239906A DD202139A5 (de)	1981-05-21	1982-05-17	Verfahren zur herstellung von dimedon

Country Status (5)

Country	Link
EP (1)	EP0065708A3 (da)
JP (1)	JPS57197239A (da)
DD (1)	DD202139A5 (da)
DK (1)	DK228182A (da)
IL (1)	IL65821A0 (da)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2261751C3 (de) *	1972-12-16	1981-12-24	Hoechst Ag, 6000 Frankfurt	Verfahren zur Herstellung von Cyclohexandionen-(1,3)
DE2448677C3 (de) *	1974-10-12	1980-04-03	Hoechst Ag, 6000 Frankfurt	Verfahren zur Herstellung von Cyclohexan-13-dionen bzw. 6-Alkyl-3, 4-dihydro-2-pyranonen
DE2450086C3 (de) *	1974-10-22	1981-10-08	Hoechst Ag, 6000 Frankfurt	Verfahren zur Herstellung von Resorcinen aus δ -Ketocarbonsäuren oder ihren Lactonen
DE2533920C2 (de) *	1975-07-30	1982-12-09	Hoechst Ag, 6000 Frankfurt	Verfahren zur Herstellung von Resorcinen

1982
- 1982-05-12 EP EP82104157A patent/EP0065708A3/de not_active Withdrawn
- 1982-05-17 DD DD82239906A patent/DD202139A5/de unknown
- 1982-05-19 DK DK228182A patent/DK228182A/da not_active Application Discontinuation
- 1982-05-19 IL IL65821A patent/IL65821A0/xx unknown
- 1982-05-20 JP JP57085649A patent/JPS57197239A/ja active Pending

Also Published As

Publication number	Publication date
EP0065708A3 (de)	1983-01-26
IL65821A0 (en)	1982-08-31
DK228182A (da)	1982-11-22
EP0065708A2 (de)	1982-12-01
JPS57197239A (en)	1982-12-03

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