CA1095089A - Procede d'obtention et emploi de cyclohexene-(1)- dione-(3,6)-tetraalkyl dicetals - Google Patents

Procede d'obtention et emploi de cyclohexene-(1)- dione-(3,6)-tetraalkyl dicetals

Info

Publication number: CA1095089A
Authority: CA; Canada
Prior art keywords: dione; cyclohexene; diketal; tetramethyl; hydroquinone
Prior art date: 1977-01-28
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

CA348,324A

Other languages

English (en)

Inventor

Rudolf Pistorius

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.)

Hoechst AG

Original Assignee

Hoechst 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.)

1977-01-28

Filing date

1980-03-24

Publication date

1981-02-03

1977-01-28 Priority claimed from DE19772703453 external-priority patent/DE2703453A1/de

1980-03-24 Application filed by Hoechst AG filed Critical Hoechst AG

1980-03-24 Priority to CA348,324A priority Critical patent/CA1095089A/fr

1981-02-03 Application granted granted Critical

1981-02-03 Publication of CA1095089A publication Critical patent/CA1095089A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title 1
-1 hydroquinone dialkyl ether Chemical class 0.000 claims abstract description 11
238000000034 method Methods 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 7
230000008569 process Effects 0.000 claims abstract description 7
QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 abstract description 11
239000000543 intermediate Substances 0.000 abstract description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 23
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000003054 catalyst Substances 0.000 description 12
235000013350 formula milk Nutrition 0.000 description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
239000001257 hydrogen Substances 0.000 description 11
229910052739 hydrogen Inorganic materials 0.000 description 11
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 9
238000005984 hydrogenation reaction Methods 0.000 description 9
239000002253 acid Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
ZROGCHDPRZRKTI-UHFFFAOYSA-N 1,4-dibutoxybenzene Chemical compound CCCCOC1=CC=C(OCCCC)C=C1 ZROGCHDPRZRKTI-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
238000004821 distillation Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000010531 catalytic reduction reaction Methods 0.000 description 3
230000007717 exclusion Effects 0.000 description 3
239000007789 gas Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000007858 starting material Substances 0.000 description 3
QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
CRUILBNAQILVHZ-UHFFFAOYSA-N 1,2,3-trimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1OC CRUILBNAQILVHZ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000000975 dye Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000004065 semiconductor Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000001052 yellow pigment Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VWGNFIQXBYRDCH-UHFFFAOYSA-N 1,4-diethoxybenzene Chemical compound CCOC1=CC=C(OCC)C=C1 VWGNFIQXBYRDCH-UHFFFAOYSA-N 0.000 description 1
JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 description 1
JNGDCMHTNXRQQD-UHFFFAOYSA-N 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarbonitrile Chemical compound O=C1C(C#N)=C(C#N)C(=O)C(C#N)=C1C#N JNGDCMHTNXRQQD-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
210000003298 dental enamel Anatomy 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
PYZLRNMGUBDIHK-UHFFFAOYSA-N molecular hydrogen;nickel Chemical compound [Ni].[H][H] PYZLRNMGUBDIHK-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229940030010 trimethoxybenzene Drugs 0.000 description 1
239000002351 wastewater Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA348,324A 1977-01-28 1980-03-24 Procede d'obtention et emploi de cyclohexene-(1)- dione-(3,6)-tetraalkyl dicetals Expired CA1095089A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA348,324A CA1095089A (fr)	1977-01-28	1980-03-24	Procede d'obtention et emploi de cyclohexene-(1)- dione-(3,6)-tetraalkyl dicetals

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DEP2703453.3		1977-01-28
DE19772703453 DE2703453A1 (de)	1977-01-28	1977-01-28	Cyclohexen-(1)-dion-(3,6)-tetraalkyldiketale, verfahren zu deren herstellung und ihre verwendung
CA295,795A CA1093586A (fr)	1977-01-28	1978-01-27	Procede d'obtention et emploi de cyclohexene-(1)- dione-(3,6)-tetraalkyldicetals
CA348,324A CA1095089A (fr)	1977-01-28	1980-03-24	Procede d'obtention et emploi de cyclohexene-(1)- dione-(3,6)-tetraalkyl dicetals

Publications (1)

Publication Number	Publication Date
CA1095089A true CA1095089A (fr)	1981-02-03

Family

ID=27165483

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA348,324A Expired CA1095089A (fr)	1977-01-28	1980-03-24	Procede d'obtention et emploi de cyclohexene-(1)- dione-(3,6)-tetraalkyl dicetals

Country Status (1)

Country	Link
CA (1)	CA1095089A (fr)

1980
- 1980-03-24 CA CA348,324A patent/CA1095089A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-02-03	MKEX	Expiry

Publication	Publication Date	Title
Baran	1960	Method for the cleavage of osmate esters
Danishefsky et al.	1979	Synthesis of disodium prephenate and disodium epiprephenate. Stereochemistry of prephenic acid and an observation on the base-catalyzed rearrangement of prephenic acid to p-hydroxyphenyllactic acid
Burness	1956	β-Keto Acetals. II. Synthesis of 3-Methyl-and 3-Phenyl-furans
CA1093586A (fr)	1981-01-13	Procede d'obtention et emploi de cyclohexene-(1)- dione-(3,6)-tetraalkyldicetals
CA1095089A (fr)	1981-02-03	Procede d'obtention et emploi de cyclohexene-(1)- dione-(3,6)-tetraalkyl dicetals
DE69103966T2 (de)	1995-03-30	Verfahren zur Herstellung von Beta-Carotin und für dieses Verfahren verwendbare Zwischenprodukte.
US5576465A (en)	1996-11-19	Process for preparing unsaturated ethers
US4278808A (en)	1981-07-14	Method of preparing a 3-alkoxy-2-alkyl-propionic acid ester derivative and intermediate therefor
US4161614A (en)	1979-07-17	Process for the preparation of cyclohexane dione-(1,4)-tetramethyl diketal
US3287372A (en)	1966-11-22	Process and intermediates for manufacture of 2-(dialkylmethyl)-5-alkyl-2-cyclohexen-1-ones
US2972631A (en)	1961-02-21	Preparation of verbenyl compounds
RU2247707C2 (ru)	2005-03-10	Способ получения 4-метоксиметил-2,3,5,6-тетрафторбензолметанола
ES2276753T5 (es)	2010-07-15	Un proceso para producir 3,7-dimetil-6-octenol opticamente activo y proceso para producir un intermedio del mismo.
US4506102A (en)	1985-03-19	2-Methoxyethyl cyclododecenyl ether and processes for its preparation and conversion to 2-methoxyethyl cyclododecyl ether
US3978135A (en)	1976-08-31	Preparation of ethers from citronellal or homologues thereof
US4204076A (en)	1980-05-20	Hydroquinone dimethyl ether
Hudson et al.	1957	The reaction of aldehydes with 4-methyl-4-penten-2-ol and α-terpineol
US3331856A (en)	1967-07-18	Method of preparing transhexahydroindanones
US6002062A (en)	1999-12-14	Process for the preparation of ethynylcyclopropane
US3085107A (en)	1963-04-09	Cyclododecylacetic acid esters, derivatives thereof and intermediates therefor
US4197411A (en)	1980-04-08	Bicyclic aldehydes
EP0019374B1 (fr)	1984-07-04	Procédé de recyclage de sous-produits pendant la production d'esters d'acide 3.3-diméthyl-4-penténoique contenant des alcoyls inférieurs
US4021491A (en)	1977-05-03	Manufacture of 2,6,6-trimethyl-cyclohex-2-en-1-one
CA1095088A (fr)	1981-02-03	Procede d'obtention de cyclohexanedione-(1,4)- tetramethyl dicetals
Hauser et al.	1957	Reactions of Methiodides of Certain exo-Methylenecyclohexadieneamines with Sodium Amide. Relation to ortho Substitution Rearrangement1