PL198498B1 - New compound, furyl analogue of farnesol - Google Patents

Abstract

The new compound, 9-furan-2-yl-3,7-dimethyl-nona-2,6-dien-1-ol of formula 1.

Description

Description of the invention

The present invention relates to a novel compound, farnesol furyl analogue, with a floral aroma similar to that of a flowering lupine.

Farnesol is an acyclic sesquiterpene alcohol found in nature, incl. in petitgrain Bigarade and ambret oil. It is widely used in flavor compositions and food flavors, and also exhibits high biological activity against pathogenic microflora.

The invention relates to a novel compound 9-furan-2-yl-3,7-dimethyl-nona-2,6-dien-1-ol of the formula I, which is a furyl analog of farnesol containing, in place of the isobutenyl group of farnesol, a furyl residue. The compound according to the invention is characterized by a pleasant, intense odor similar to that emitted by the flowers of yellow lupine, its volatility is much lower than that of farnesol, and moreover, it exhibits higher solubility in hydroalcoholic solvents than farnesol, which is a desirable property from the point of view of application in agents perfumery. The new compound is used as a component of fragrances imitating natural floral and fancy fragrances. The physicochemical spectral properties of the new compound are as follows: boiling point 398-400 K at a pressure of 0.07 kPa;

MS (cis / cis isomer): 234 (M ⁺ , 3), 216 (4), 149 (6), 134 (7), 122 (8), 107 (8), 93 (13), 82 (11) . 81 (100), 53 (28), 41 (17);

MS (cis / trans isomer): 234 (M ⁺ , 4), 216 (6), 135 (8), 122 (20), 107 (18), 93 (36), 82 (32), 81 (100) . 53 (52), 41 (35);

MS (trans / cis isomer): 234 (M ⁺ , 2), 216 (4), 149 (7), 122 (10), 107 (11), 93 (18), 82 (20), 81 (100) . 53 (40), 41 (28);

MS (trans / trans isomer): 234 (M ⁺ , 4), 216 (6), 122 (13), 107 (16), 93 (25), 82 (36), 81 (100), 67 (24) 53 (52), 41 (38).

¹ H NMR (CDCl3) δ: 7.28 (m, 1H), 6.27 (m, 1H), 5.96 (m, 1H), 5.40 (m, 1H), 5.14 (m , 1H), 4.12 (m, 2H), 2.70 (m, 2H), 2.34 (m, 2H), 2.06 (m, 4H), 1.76, 1.70, 1, 68, 1.66 (4s, 6H).

9-Furan-2-yl-3,7-dimethyl-nona-2,6-dien-1-ol of formula 1 can be obtained as a mixture of four cis / trans isomers from 5-furan-2-yl-3 -methylpent-1-en-3-ol of formula 2, which is treated in the first step with ethyl acetoacetate. The ketone formed in this reaction is subjected to a Grignard reaction with vinylmagnesium bromide and then to phosphorus tribromide (PBr3) to form a bromine derivative which is treated with potassium acetate to form 9-furan-2-yl acetate. 3,7-dimethyl-nona-2,6-dien-1-ol. Alkaline hydrolysis of this acetate gives 9-furan-2-yl-3,7-dimethyl-nona-2,6-dien-1-ol with a yield of about 50%, based on the starting compound of formula II.

The following example illustrates the subject of the invention.

P r z k ł a d

A mixture of 0.1 mol of 5-furan-2-yl-3-methylpent-1-en-3-ol and 0.2 mol of ethyl acetoacetate was heated to 180 ° C for 3 hours. During the reaction, carbon dioxide was released and ethanol was distilled off. After completion of the reaction, excess ethyl acetoacetate was evaporated and then the reaction product was distilled off at a boiling point of 380-393 K at 0.53 kPa. 0.048 mol of the obtained ketone was added dropwise over 2 hours to a solution of 0.05 mol of vinylmagnesium bromide in 50 ml of tetrahydrofuran while maintaining the temperature at about 35 ° C. After completion of the reaction, saturated ammonium chloride solution was added and the product was extracted three times with toluene. The product extract, after washing with water and evaporating the solvent, was distilled at 383-393 K at 0.67 kPa. To a mixture of 0.04 mole of the alcohol obtained in 60 cm ^{3 of} diethyl ether, cooled to -20 ° C, 0.03 mole of PBr3 was added dropwise with stirring. After completion of the dropwise addition, the contents of the flask were stirred at this temperature for 1.5 hours, then the reaction mixture was poured into 40 cm ^{3 of} water and the layers were separated. The organic layer was washed 3 times with 25 cm ³ of water, 50 cm ^{3 of} a 1% solution of Na2S2O4, dried again with water. After distilling off the ether to the residue was added 70 cm ^{3 of} dimethylformamide and 0.03 mole of potassium acetate, and the mixture was heated mix pbw 1.5 hours at 95 ° C. After cooling, 70 cm ^{3 of} diethyl ether were added to the mixture, the organic layer was washed neutral with water, dried and then distilled. 0.03 mol of the resulting mixture of cis / trans acetates furyloanalogów farnesol was heated for 3 hours under reflux with 0.03 mole of KOH and 25 cm ³ of methanol. After cooling, the mixture was poured into 15 cm ^{3 of} water

The mixture was extracted with 5 portions of methylene chloride. The combined organic layers were washed with neutral pH, dried and distilled.

A mixture of the four cis / trans furyl analogs of the formula I with the above-mentioned physicochemical and spectral properties was obtained with a yield of 85%.

Claims (1)

Patent claim The new compound, 9-furan-2-yl-3,7-dimethyl-nona-2,6-dien-1-ol of formula 1.