JPH0257553B2 - - Google Patents

Info

Publication number: JPH0257553B2
Authority: JP; Japan
Prior art keywords: cineole; reaction; mentene; hexane; observed
Prior art date: 1987-04-09
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

JP62085833A

Other languages

English (en)

Japanese (ja)

Other versions

JPS63253081A (ja

Inventor

Yoshiharu Matsubara

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.)

JNC Corp

Original Assignee

Chisso Corp

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.)

1987-04-09

Filing date

1987-04-09

Publication date

1990-12-05

1987-04-09 Application filed by Chisso Corp filed Critical Chisso Corp

1987-04-09 Priority to JP62085833A priority Critical patent/JPS63253081A/ja

1988-10-20 Publication of JPS63253081A publication Critical patent/JPS63253081A/ja

1990-12-05 Publication of JPH0257553B2 publication Critical patent/JPH0257553B2/ja

Status Granted legal-status Critical Current

Links

HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 claims description 9
230000002378 acidificating effect Effects 0.000 claims description 9
238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims description 6
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 5
JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
230000001590 oxidative effect Effects 0.000 claims description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
239000003921 oil Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
238000001819 mass spectrum Methods 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
-1 vinyl methyl Chemical group 0.000 description 8
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
238000004817 gas chromatography Methods 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
239000000203 mixture Substances 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
150000001793 charged compounds Chemical class 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WEEGYLXZBRQIMU-UHFFFAOYSA-N Eucalyptol Chemical compound C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
HTGSXANWVMWFEM-UDNWOFFPSA-N [(2s)-2,4-dimethyl-3-oxabicyclo[2.2.2]octan-2-yl]methanol Chemical compound C1CC2[C@@](C)(CO)OC1(C)CC2 HTGSXANWVMWFEM-UDNWOFFPSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
239000012634 fragment Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 3
229910000343 potassium bisulfate Inorganic materials 0.000 description 3
FAMJUFMHYAFYNU-UHFFFAOYSA-N 1-methyl-4-(propan-2-yl)cyclohex-1-ene Chemical compound CC(C)C1CCC(C)=CC1 FAMJUFMHYAFYNU-UHFFFAOYSA-N 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 2
239000003905 agrochemical Substances 0.000 description 2
150000001336 alkenes Chemical group 0.000 description 2
MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
230000017858 demethylation Effects 0.000 description 2
238000010520 demethylation reaction Methods 0.000 description 2
VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
XMFOQHDPRMAJNU-UHFFFAOYSA-N lead(ii,iv) oxide Chemical compound O1[Pb]O[Pb]11O[Pb]O1 XMFOQHDPRMAJNU-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000000034 method Methods 0.000 description 2
CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane Chemical class CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 2
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
230000002194 synthesizing effect Effects 0.000 description 2
150000000193 1,8-cineol derivatives Chemical class 0.000 description 1
JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 description 1
239000001293 FEMA 3089 Substances 0.000 description 1
230000005526 G1 to G0 transition Effects 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
241001271990 Tomicus piniperda Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000002131 composite material Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
230000002250 progressing effect Effects 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000005871 repellent Substances 0.000 description 1
230000002940 repellent Effects 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Pyrane Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

JP62085833A 1987-04-09 1987-04-09 １，８−シネオ−ル−９−置換体及びその製造方法 Granted JPS63253081A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP62085833A JPS63253081A (ja)	1987-04-09	1987-04-09	１，８−シネオ−ル−９−置換体及びその製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP62085833A JPS63253081A (ja)	1987-04-09	1987-04-09	１，８−シネオ−ル−９−置換体及びその製造方法

Publications (2)

Publication Number	Publication Date
JPS63253081A JPS63253081A (ja)	1988-10-20
JPH0257553B2 true JPH0257553B2 (th)	1990-12-05

Family

ID=13869853

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP62085833A Granted JPS63253081A (ja)	1987-04-09	1987-04-09	１，８−シネオ−ル−９−置換体及びその製造方法

Country Status (1)

Country	Link
JP (1)	JPS63253081A (th)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19608316C2 (de) *	1996-02-22	2000-11-09	Ivoclar Ag Schaan	Funktionalisierte bicyclische (Meth)acrylate, Verfahren zu deren Herstellung und deren Verwendung ####

1987
- 1987-04-09 JP JP62085833A patent/JPS63253081A/ja active Granted

Also Published As

Publication number	Publication date
JPS63253081A (ja)	1988-10-20

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