JPH07291883A - Ether compound and perfume composition containing the same - Google Patents

Abstract

PURPOSE:To obtain a new ether compound useful as a perfume preparing material having a floral or green-tone fragrance. CONSTITUTION:A compound of the formula ((n) is 1 or 2; R1 is CH3, C2H5 or C3H7; R2 is CH3 or C2H5) such as 2-methoxybenzyl methyl ether. The compound of the formula, for example, is obtained by reacting 4-methoxybenzyl alcohol with methyl iodide in a solvent such as DMF at room temperature. A perfume composition is obtained by containing the compound of the formula.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel ether compound useful as a perfume material and a fragrance composition containing the compound.

[0002]

2. Description of the Related Art With the progress of synthetic organic chemistry, the number of compounds that can be used as a fragrance has increased dramatically, and the number of compounds is 3,0 now.
It is also said that there are 00 types and 5,000 types. Of these, ether compounds generally have a weak fragrance, and therefore the number of types of compounds used as fragrances is very small under the present circumstances.

As ether compounds which are widely used as a fragrance at present, first of all, as an aliphatic compound, forest-like ceryl methyl ether and camphor-like 1,8-cineole are known. On the other hand, as an aromatic compound, anise-like anethole, spicy methyl chavicol, methyl eugenol and the like are known. However, as can be seen from the scents of these compounds, in general, the scents of ether compounds are poor in floral and green tones, which should be said to be the most important factors when formulating a fragrance. Further, particularly in the case of a compound having an unsaturated bond such as a double bond in the structure, the characteristics of the chemically stable ether compound are not exerted, and the addition reaction of halogen or water to the unsaturated bond, the substitution There is a possibility that a reaction, a polymerization reaction of an unsaturated bond, etc. may occur, and the aroma inherent in the compound is likely to be impaired.

[0004]

SUMMARY OF THE INVENTION In view of the above situation, an object of the present invention is to provide a fragrance material having a floral and green persistent fragrance and further excellent stability. is there.

[0005]

Means for Solving the Problems In searching for aroma components of various plants for the purpose of developing a new fragrance material, the inventors of the present invention, Muscari-Armeniacum (Muscari) native to the Mediterranean region and Southwest Asia armeniacum
Leichtl. ex Bak. ) Focused on the persistent and strong unique scent, and conducted a component study. As a result, as the main component of this flower essential oil, the following formula (II)

[0006]

[Chemical 2]

4-methoxyphenethyl methyl ether represented by the following formula was discovered, and further studies were conducted to reach the present invention.

The present invention has the following formula (I)

[0009]

[Chemical 3]

In the formula, n is 1 or 2, R ₁ is CH ₃ , C ₂ H
₅ or C ₃ H ₇ , R ₂ represents CH ₃ or C ₂ H ₅ , and a novel ether compound represented by the following, and a perfume composition containing the ether compound.

The ether compound of the present invention has a floral or green odor and is useful as a novel fragrance material.

The ether compound of the present invention can be synthesized as a single product using commercially available compounds such as 4-methoxybenzyl alcohol and 4-methoxyphenethyl alcohol.

The odor characteristics, IR and MS data of the ether compound of the present invention are shown below.

[0014]

[Table 1]

[0015]

[Table 2]

[0016]

[Table 3]

[0017]

[Table 4]

[0018]

[Table 5]

[0019]

[Table 6]

[0020]

[Table 7]

[0021]

[Table 8]

[0022]

[Table 9]

[0023]

[Table 10]

[0024]

[Table 11]

[0025]

[Table 12]

The ether compound of the present invention has excellent organoleptic properties and stability when blended in a perfume composition used for perfumes, colognes, shampoos, rinses, lotions, soaps, detergents, fragrances, bath agents and the like. Can be a product.

When the ether compound of the present invention is used for the production of a fragrance composition, the compounding amount thereof is usually selected in the range of 0.1 to 30% by weight, but depending on the intended sensory effect, it may be used outside this range. You can. The fragrance composition to be blended with the ether compound of the present invention is not particularly limited, and a suitable fragrance composition such as a compounded fragrance composition usually used for the above-mentioned applications can be used.

The present invention will be described in more detail with reference to synthetic examples and examples, but the present invention is not limited thereto.

[0029]

【Example】

Synthesis Example 1 Synthesis of 4-methoxybenzyl methyl ether 4-methoxybenzyl alcohol 6 g (0.043mo
l) was dissolved in 80 ml of N, N-dimethylformamide to give 1.978 g (0.086 g · at) of sodium metal.
m. ) Was added and the mixture was stirred at room temperature for 1 hour and 30 minutes. After the reaction, 9.159 g (0.064 mol) of methyl iodide was added to N,
What melt | dissolved in 40 ml of N-dimethylformamide was dripped, it stirred at room temperature for 5 hours, after reaction, after adding diethyl ether and wash | cleaning by a saturated salt solution, the ether layer was collect | recovered under reduced pressure and 4.276 g of crude products were Obtained. Further, the crude product was purified to obtain 1.961 g of 4-methoxybenzyl methyl ether. (Yield 30.0 mol%) The structure was confirmed by IR and MS.

Synthesis Example 2 Synthesis of 4-methoxyphenethyl methyl ether 10 g (0.066) of 4-methoxyphenethyl alcohol
mol), 150 ml of N, N-dimethylformamide
Dissolved in 2.270 g (0.099 g) of sodium metal
-Atm. ) Was added and the mixture was stirred at room temperature for 1 hour and 30 minutes. After the reaction, 14.20 g (0.099 mol) of methyl iodide
Was dissolved in 50 ml of N, N-dimethylformamide, and the mixture was stirred at room temperature for 5 hours. After the reaction, diethyl ether was added and the mixture was washed with saturated brine, and the ether layer was collected under reduced pressure to obtain a crude product. 6.530 g was obtained.
Further, the crude product was purified to obtain 2.860 g of 4-methoxyphenethyl methyl ether. (Yield 26.10mo
1%) structure was confirmed by IR and MS.

Example 1 The following components were mixed as a carnation type blended fragrance composition. Eugenol 430 Cynamic alcohol 150 Hexyl salicylate 60 Vanillin 10 Heliotropin 20 Phenylpropylaldehyde 5 Phenylethyl alcohol 15 Geraniol 15 Citronellol 10 Geranyl acetate 5 Benzylacetate 10 Cyclopentadecanolide 20 Total 750 750 g of 2-ethoxybenzylmethyl in the above composition. By adding 250 g of ether, an excellent fragrance composition having natural carnation characteristics could be obtained.

Example 2 The following components were mixed as a natural rose type compounded fragrance composition. Citronellol 300 Geraniol 190 Methyleugenol 15 Phenylethyl alcohol 120 Phenylethyldimethylcarbinol 5 Phenylethylacetate 20 β-Ionone 10 Geranium oil 15 Undecylenealdehyde 1 Rosephenone 10 cis-3-Hexenol 10% (Diisoptyl adipate) 4 Cyclopenta Decanolide 10 Total 700 By adding 100 g of 2-ethoxybenzyl ethyl ether to 700 g of the above composition, an excellent fragrance composition having pollen-like elements of natural rose could be obtained.

Example 3 The following components were mixed as a hyacinth-type mixed fragrance composition. Phenylethyl alcohol 300 Terpineol 150 Cynamic alcohol 100 Hexyl cinnamic aldehyde 50 Phenylethyl salicylate 100 Phenylacetaldehyde Dimethyl acetal 30 Eugenol 20 Benzyl acetate 20 Galvanum oil 10% (Dipropylene glycol) 30 Indole 10 Heliotropin 5 Cyclopentadecanolide 5 820 total 820 g of the composition 820 g of 4-methoxyphenethyl methyl ether 80 g and 4-ethoxybenzyl methyl ether 2
By adding 0 g, an excellent fragrance composition of fresh natural green note, which is a characteristic of hyacinth flowers, could be obtained.

[0034]

The ethers having methoxyphenyl and ethoxyphenyl groups of the present invention and the fragrance composition containing them are excellent materials that give a preferable effect as a fragrance material, and the fragrance composition can be obtained conventionally. It has a unique scent that could not be done.

[Brief description of drawings]

FIG. 1 is an MS spectrum diagram of 2-methoxyphenylethyl methyl ether.

FIG. 2 MS of 3-methoxyphenethyl methyl ether
Spectral diagram.

FIG. 3 MS of 4-methoxyphenethyl methyl ether
Spectral diagram.

FIG. 4 MS of 2-methoxyphenethyl ethyl ether
Spectral diagram.

FIG. 5 MS of 3-methoxyphenethylethyl ether
Spectral diagram.

FIG. 6 MS of 4-methoxyphenethylethyl ether
Spectral diagram.

FIG. 7: IR of 4-methoxyphenethyl methyl ether
Spectral diagram.

Claims (2)

[Claims] 1. The following formula (I): In the formula, n is 1 or 2, R ₁ is CH ₃ , C ₂ H ₅ or C ₃ H
₇ , an ether compound represented by R ₂ is CH ₃ or C ₂ H ₅ . 2. A perfume composition containing the compound according to claim 1.