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SU618374A1 - 4-methyl-2-(2,6-dimethylheptadiene-1,5-yl-1)-tetrahydropyranol-4 as fragrant substance for perfumery compositions - Google Patents

4-methyl-2-(2,6-dimethylheptadiene-1,5-yl-1)-tetrahydropyranol-4 as fragrant substance for perfumery compositions

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Publication number
SU618374A1
SU618374A1 SU772457984A SU2457984A SU618374A1 SU 618374 A1 SU618374 A1 SU 618374A1 SU 772457984 A SU772457984 A SU 772457984A SU 2457984 A SU2457984 A SU 2457984A SU 618374 A1 SU618374 A1 SU 618374A1
Authority
SU
USSR - Soviet Union
Prior art keywords
methyl
tetrahydropyranol
mol
dimethylheptadiene
ether
Prior art date
Application number
SU772457984A
Other languages
Russian (ru)
Inventor
Александр Амбарцумович Геворкян
Пепроне Ивановна Казарян
Галина Григорьевна Филатова
Валентина Рафаиловна Зананьянц
Original Assignee
Институт Органической Химии Ан Армянской Сср
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.)
Filing date
Publication date
Application filed by Институт Органической Химии Ан Армянской Сср filed Critical Институт Органической Химии Ан Армянской Сср
Priority to SU772457984A priority Critical patent/SU618374A1/en
Application granted granted Critical
Publication of SU618374A1 publication Critical patent/SU618374A1/en

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  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)

Claims (1)

(54) 4-МЕТИЛ-2-(2,6-ДИМЕТИЛГЕПТАДИЕН-1,5-ИЛ-1)-ТЕТРАГИДРОПИРАНОЛ-4 В КАЧЕСТВЕ ДУШИСТОГО ВЕЩЕСТВА ДЛЯ ПАРФЮМЕРНЫХ КОМПОЗИЦИЙ Пример. 4-метил-2--(2,6-диме тилгвптадивн-1,5-ил-1)-твтрагидропи ранол-4,.Л. Смесь 7,6 г {0,05 моль) цитрал , 4.3 г (0,05 моль) 2-мвтилбутен-1-ола-4- и 2 мл серной кисло перемешивают 4 ч при ЗО-бО С, нейтр лизуют поташом, экстрагируют эфиром высушивают над сульфатом магни . После отгонки растворител  разгоикой в вакууме выдел ют 6,7 г (56.2%) продукта,т.кип.176-1eo C/lO П I,4925jcl5 0,9839, Найдено,%«С 75,42 Н 10,85. Вычислено,%j С 75,62) Н 10,91. Смесь 7,6 г (0,05 моль) цитрал , 4,3 г (0,05 моль) 2-метилбутен-1-ала-4 ,3 мл воды и 2-2,5 г ионообменной смолы КУ-1 в Н-форме перемешивают 6 ч при ЗО-бО С. Затем катализатор промывают эфиром, водный сло экстрагируют эфиром, объединенные эфирные выт жки сушат над сульфатом магни . После удалени  растворител  выдел ют 6,9 г (58,1%) продукта, т.кип. - в ИК-спектрах образцов присутствуют характерные полосы поглощени  ОН-группы при 3590-3345 см и С«С св зи при 1670-1655 см Доступность и дешевизна исходного 2-метилбутен-1--ола-4,  вл ющегос  многотоннажным промежуточным продуктом при производстве изопрена по Принсу, простота синтеза 4-метил-2 (2,6-диметилгептадиен-1,5-ил-1)- Тетрагидропиранола-4 , получаемого с высоким выходом, позвол ет создавать дешевые парфюмерные композиции. Формула изобретени  4-Метил-2-(2,6-диметилгептадиен-1 ,5-ИЛ-1)-тетрагидропиранол-4 формулы d он UC 0(Н(-СН2-(Нг-( в качестве душистого вещества дп  парфюмерных композиций. Источники информации, прин тые во нимание при экспертизе: 1. За вка №2140700/23-04, л. С 07 I 309/12, 03.06.75, по коорой прин то решение о выдаче авторкого свидетельства.(54) 4-METHYL-2- (2,6-DIMETHYL-HEPTADIEN-1,5-IL-1) -TETRAHYDROPYRANOL-4 AS A DELICATE SUBSTANCE FOR PERFUME COMPOSITIONS Example. 4-methyl-2 - (2,6-dime tylgvptadivn-1,5-yl-1) -tragidropi ranol-4, .L. A mixture of 7.6 g {0.05 mol) citral, 4.3 g (0.05 mol) 2-mbutyl-1-ol-4- and 2 ml of sulfuric acid is stirred for 4 hours at 30 ° C, the substrate is lysed with potash, extracted ether is dried over magnesium sulphate. After distillation of the solvent by distillation, 6.7 g (56.2%) of the product were isolated in vacuo, bp 176-1eo C / lO P I, 4925jcl5 0.9839, Found,% C 75.42 H 10.85. Calculated,% j C 75.62) H 10.91. A mixture of 7.6 g (0.05 mol) citral, 4.3 g (0.05 mol) of 2-methylbutene-1-ala-4, 3 ml of water and 2-2.5 g of the ion-exchange resin KU-1 in H -form the mixture for 6 hours at 30A-C. Then the catalyst is washed with ether, the aqueous layer is extracted with ether, and the combined ether extracts are dried over magnesium sulfate. After removal of the solvent, 6.9 g (58.1%) of product was isolated, b.p. - in the IR spectra of the samples, there are characteristic absorption bands of the OH group at 3590-3345 cm and С "С communication at 1670-1655 cm. Availability and low cost of the initial 2-methylbutene-1 - ol-4, which is a large intermediate product at the production of isoprene according to Prince, the simplicity of the synthesis of 4-methyl-2 (2,6-dimethylheptadiene-1,5-yl-1) -Tetrahydropyranol-4, obtained in high yield, allows you to create cheap perfume compositions. Claims of the invention 4-Methyl-2- (2,6-dimethylheptadiene-1, 5-IL-1) -tetrahydropyranol-4 of the formula d it is UC 0 (H (-CH 2- (Ng- (as a fragrance dp perfume compositions. Sources of information taken into account in the examination: 1. Application No. 2140700 / 23-04, L. 07 I 309/12, 03.06.75, which coordinated the decision to issue a copyright certificate.
SU772457984A 1977-03-01 1977-03-01 4-methyl-2-(2,6-dimethylheptadiene-1,5-yl-1)-tetrahydropyranol-4 as fragrant substance for perfumery compositions SU618374A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
SU772457984A SU618374A1 (en) 1977-03-01 1977-03-01 4-methyl-2-(2,6-dimethylheptadiene-1,5-yl-1)-tetrahydropyranol-4 as fragrant substance for perfumery compositions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SU772457984A SU618374A1 (en) 1977-03-01 1977-03-01 4-methyl-2-(2,6-dimethylheptadiene-1,5-yl-1)-tetrahydropyranol-4 as fragrant substance for perfumery compositions

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SU618374A1 true SU618374A1 (en) 1978-08-05

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0383446A2 (en) * 1989-02-09 1990-08-22 INTERNATIONAL FLAVORS & FRAGRANCES INC. 2,4,4-Trisubstituted tetrahydropyranyl esters and organoleptic uses thereof
US4962090A (en) * 1990-03-22 1990-10-09 International Flavors & Fragrances Inc. 2,4-disubstituted and 2,2,4-trisubstituted tetrahydropyranyl-4-ethers, process for preparing same and perfumery uses thereof
US4999439A (en) * 1990-03-22 1991-03-12 International Flavors & Fragrances Inc. Alkyl-substituted tetra- or hexahydrobenzopyran derivatives, organoleptic uses thereof and process for preparing same
US5023352A (en) * 1990-03-22 1991-06-11 International Flavors & Fragrances Inc. Alkyl-substituted tetra- or hexahydrobenzopyran derivatives, organoleptic uses thereof and process for preparing same
US5030618A (en) * 1990-03-22 1991-07-09 International Flavors And Fragrances Inc. Alkyl-substituted tetra- or hexahydrobenzopyran derivatives, organoleptic uses thereof and process for preparing same
CN105164110A (en) * 2013-04-29 2015-12-16 巴斯夫欧洲公司 Method for producing 2-substituted 4-hydroxy-4-methyl-tetrahydropyrans in a reactor cascade

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0383446A2 (en) * 1989-02-09 1990-08-22 INTERNATIONAL FLAVORS & FRAGRANCES INC. 2,4,4-Trisubstituted tetrahydropyranyl esters and organoleptic uses thereof
US4963285A (en) * 1989-02-09 1990-10-16 International Flavors & Fragrances Inc. 2,4,4-irisubstituted tetrahydro pyranyl esters and organoleptic uses thereof
US4962090A (en) * 1990-03-22 1990-10-09 International Flavors & Fragrances Inc. 2,4-disubstituted and 2,2,4-trisubstituted tetrahydropyranyl-4-ethers, process for preparing same and perfumery uses thereof
US4999439A (en) * 1990-03-22 1991-03-12 International Flavors & Fragrances Inc. Alkyl-substituted tetra- or hexahydrobenzopyran derivatives, organoleptic uses thereof and process for preparing same
US5023352A (en) * 1990-03-22 1991-06-11 International Flavors & Fragrances Inc. Alkyl-substituted tetra- or hexahydrobenzopyran derivatives, organoleptic uses thereof and process for preparing same
US5030618A (en) * 1990-03-22 1991-07-09 International Flavors And Fragrances Inc. Alkyl-substituted tetra- or hexahydrobenzopyran derivatives, organoleptic uses thereof and process for preparing same
CN105164110A (en) * 2013-04-29 2015-12-16 巴斯夫欧洲公司 Method for producing 2-substituted 4-hydroxy-4-methyl-tetrahydropyrans in a reactor cascade
CN105164110B (en) * 2013-04-29 2019-01-22 巴斯夫欧洲公司 Process for the preparation of 2-substituted 4-hydroxy-4-methyltetrahydropyrans in a reactor cascade

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