SU620487A1 - 4-methyl-2-hexyltetrahydropyranol-4 as fragrant substance for perfumery - Google Patents

Description

Chelation is a new compound - 4-megip-2-hexa-agragidropcranop-4 of formula I. N. .HE

Which can be used as a fragrant substance, reminiscent of the smell of a nasturtium flower, for the guy fk) MepHbix compositions.

A fragrant substance is known: 2,4-6-trimetip-2-isobutenip-3, 6-dihydr1-pyran, obtained from 2-metipectenopa-4 and mesitype oxide by boiling for 24 hours in an aqueous medium in the presence of sulfuric acid in 25% yield j.

However, the widespread use of this compound prevents the availability of starting materials.

In addition, 4-metip-2-prop-niptetrahydropyranop-4-4 is known, which is used as a fragrant substance with the smell of peps 2.,

The chain of the invention is the preparation of a novel compound of the formula 1 - 4-metip-2-gen-tegrahydropyranopa-4 as a fragrant substance with a new shade of smell.

The method of preparing the compound of formula I is that the 2-methiputene-2-op-4 is condensed with enante aldehyde in an aqueous medium when heated in the presence of an acid catalyst.

Inorganic acids are used as acid catalysts. They are in the H form. Condensation is preferably carried out at an equimolecular ratio of the starting components. Preferably, sulfuric or phosphoric acid is used as the acid catalyst and the wire is heated at 50-60 ° C, which avoids the formation of digidropyrans.

Claims (2)

Preferably, chromic acid 2O30 is used in an amount of 10-30% by weight of the initial reagents. Carrying out the process in the presence of more diluted oxygen is accompanied by an adverse hydration reaction of 2g megip-bougain-l-orja-4 and further transformation of the latter. 4-Megip-2-propeny / 1-heghydropyranol-4, which has a smell resembling the halls of a nasturtium flower, received a rating of 4.0 by the paternal system from the partners of the Leningrad Perfume Factory of the Northern Division and a recommendation for use in cosmetic and perfumery production . Example D. 4-Methii-2-hexipte trahydropyra op-4. A. A mixture of 11.5 g (O, 1 mop) enanthic aldehyde, 8.6 g (O, 1 mop) 2-ml tilbute -1-opa-4 and 2 ml of ZO% sulfuric acid per stirring time 4 h at 560 ° C, neutralized with potash, extracted with ether, dried over magnesium sulphate. After distilling off, dissolve in vacuo to give 1O, 8 g (5O, 4% 4-metip-2-hexyltetrahydropyranol-4) with a temper of 161-165s / 22 mm pg cr.j "1. 5L - -, - 1, 4640, di 0.9453. Found,%: C 7O, 37, H ISO. C., -. (9 YJ. I Vigchi7Ino,%: C 7O, 20, H 12, OO B. Mixture 11.5 g JO , 1 mop) enanthic aldehyde, 8.6 g (OD mop) 2-me gipbuten-1-ol-4, 3 ml of water and 2 g of the KU-1 ion-exchange smopa are mixed in H-form for 6 hours at 50-6 ° С Then the reaction mixture from (1 ml) is removed, the catalyst is washed with e4ir, the aqueous layer is extracted with ether, and the combined ufira extracts are dried over magnesium sulfate. After removing the solvent in divided 11 g (55.0%) 4 Megal-2-hexylretrahydropyranol 4 with a bp 1611b5s / 22 mmHg, P 1.4640, fo, 9453 .. In the IR spectra of the samples, characteristic OH absorptions are present -groups at 352О-3340 cm. Due to the availability of starting compounds of enaitic aldehyde and 2-methylbute -1-opa-4, which is a large-tonnage I intermediate product in the production of isoprene according to Priis, the simplicity of synthesis of 4-metip-2-hexipte1 ra6ep-4 hydrohydropyne with high output, its use can create savings in the national economy. Claims. 4-Megyl-2-hexyl tetrahydropyranol-4 of formula I. n, c.on U as a fragrant substance for couples (fumer compositions. Sources of information taken into account during the examination: 1. US Patent No. 3455957, class 260. 345 1, 1969. 2. Forward number 2455528/23-О4, кп. From 07 D 309/04, 24Д32.77, according to Kt, the mountain made the decision to issue an autorgas -o certificate