JPH09111281A - Perfume composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a perfume composition, comprising a butanol derivative represented by a specific formula, having a fragrance of a sweet floral muguet note by itself and capable of imparting sweetness with volume or floral softness to the fragrance by addition thereof to other perfumes and useful as perfumery, etc. SOLUTION: This perfume composition comprises 4-(2-methoxyphenyl)-2- methyl-2-butanol of formula I. The butanol is obtained by carrying out the Reformartsky reaction of o-anisaldehyde with ethyl bromoacetate, performing the catalytic hydrogenolysis of OH group in the benzyl position of the resultant hydroxy ester in the presence of a metallic catalyst and then reacting the prepared compound with methyl-lithium according to, e.g. formula II.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a perfume composition containing 4- (2-methoxyphenyl) -2-methyl-2-butanol.

[0002]

2. Description of the Related Art There are various demands for a compounding material for a fragrance, such as a low price, chemical stability, and a new scent. Conventionally, various compounds have been known as ingredients for preparing fragrances.
It is extremely important in the preparation of perfumes.

[0003]

Under such circumstances, the inventors of the present invention have investigated the fragrances of compounds having various functional groups and their blending systems in order to find a novel compounding material for fragrances, and have found that the results of literature [eg, Bull. Soc. Chim. Beig., 90
(8), 847-848 (1981)) 4- (2-methoxyphenyl) -2-methyl-2-butanol represented by the following formula (1), which is a known compound, is added to a fragrance composition. The present invention has been completed by finding that the scent imparts a volume of sweetness and flower-like softness, and is useful as a fragrance material.

[0004]

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That is, the present invention provides the above-mentioned 4- (2-methoxyphenyl) -2-methyl-2-butanol (hereinafter referred to as "perfume compound"
(1) ”is provided as an active ingredient.

The fragrance compound (1) used in the present invention is a known compound as described above, but up to now, there has been no report on its fragrance, let alone its use as a compounded fragrance.

[0007]

BEST MODE FOR CARRYING OUT THE INVENTION The fragrance compound (1) is obtained by esterifying 2-methoxyphenylpropionic acid obtained from dihydrocoumarin and dimethylsulfate according to the description in the above-mentioned document,
It can also be produced by reacting with methylmagnesium iodide, but otherwise, for example, according to the following reaction formula, Reform of o-anisaldehyde and ethyl bromoacetate
It can also be produced by catalytically hydrolyzing the benzylic hydroxyl group of the hydroxy ester obtained by the atsky reaction in the presence of a metal catalyst, and then reacting it with methyllithium.

[0008]

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The fragrance compound (1) has a sweet, flower-like and muguet-like fragrance, and by adding the compound to other fragrances at various ratios, the fragrance has a sweetness. It is possible to give the softness of a flower and a flower.

The amount of the fragrance compound (1) to be added to the fragrance composition of the present invention varies depending on the target fragrance, the target fragrance, etc., and is not particularly limited as long as it can impart the target fragrance. However, generally 1 to 50% by weight, especially
It is preferable to add 10 to 30% by weight.

The fragrance composition of the present invention can be widely used for perfumes, soaps, shampoos, rinses, detergents, cosmetics, sprays, fragrances and the like which require perfume.

[0012]

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

Synthesis Example 1 (1) Ethyl 3- (2-methoxyphenyl) propionate: In a 300 ml three-necked flask equipped with a cooling tube and a thermometer, 17 g (125 mmol) of o-anisaldehyde and 25 parts of ethyl bromoacetate were added.
g (150 mmol), 14 g (217 mmol) of zinc powder and 42 ml of dry dioxane were added, mixed and dispersed. To this, 0.1 g of iodine was added, and ultrasonic waves were irradiated until the exothermic reaction started. The reaction mixture was stirred for 1 hour after starting the exothermic reaction while air-cooling, then poured into ice water, the insoluble matter was filtered off, and the mixture was extracted with ether. The organic layer was washed with 10% aqueous sodium thiosulfate solution and saturated brine, dried and concentrated to give 25 g of a crude product.
I got 25 g of this crude product was added to ethanol under hydrogen pressure of 3
2.5 g of palladium on activated carbon under kg / cm ² at room temperature
Hydrogenolysis was performed until the absorption of hydrogen stopped for 0 hours.
After the reaction, the catalyst was filtered off and the organic layer was concentrated and purified by silica gel column chromatography to give the title compound 2
1.2 g (102 mmol) was obtained (yield 82%).

¹ H-NMR (CDCl ₃ , 200 MHz) δ ppm: 1.23 (3 H, t, J =
7.2Hz), 2.59 (2H, t, J = 8.2Hz), 2.94 (2H, t, J = 8.2Hz), 3.8
1 (3H, s), 4.11 (2H, q, J = 7.2Hz), 6.8-6.9 (2H, m), 7.1-7.
2 (2H, m) IR (KBr, cm ^-1 ): 1740 (C = O)

(2) 4- (2-methoxyphenyl) -2-methyl-2-
Butanol synthesis: To a 500 ml four-necked flask equipped with a condenser and a thermometer, 14 g (67 mmol) of ethyl 3- (2-methoxyphenyl) propionate and 100 ml of anhydrous THF were added and dissolved, and the mixture was cooled to -78 ° C. . To this solution, 140 ml (161 mmol) of methyllithium diethyl ether solution (1.05M) was added dropwise so that the solution temperature did not exceed -40 ° C. After dropping, 3
After stirring for 0 minutes at -78 ° C, saturated ammonium chloride aqueous solution was added to stop the reaction. The organic layer is separated, washed with water, dried and concentrated to give a crude product, which is purified by silica gel column chromatography to obtain 12 g (63 mm) of the desired title compound.
ol) was obtained (94% yield).

¹ H-NMR (CDCl ₃ , 200 MHz) δ ppm: 1.30 (6 H, s),
1.56 (1H, brs), 1.70-1.80 (2H, m), 2.62-2.75 (2H, m), 3.8
4 (3H, s), 6.8-6.9 (2H, m), 7.1-7.3 (2H, m) IR (KBr, cm ^-1 ): 3400 (OH)

Example 1 Muguet type mixed fragrance

[Table 1]

By adding 200 parts by weight of 4- (2-methoxyphenyl) -2-methyl-2-butanol to 800 parts by weight of the above-prepared prepared flavor, a prepared flavor with added sweetness, softness and volume can be obtained. It was

Example 2 Blended fragrance for detergents

[Table 2]

To 200 parts by weight of 4- (2-methoxyphenyl) -2-methyl-2-butanol was added to 800 parts by weight of the above-prepared fragrance to prepare a floral muguet-like detergent with added sweetness and softness. A fragrance was obtained.

[0021]

EFFECTS OF THE INVENTION The fragrance compound (1) itself has a sweet, flower-like and muguet fragrance. By adding the compound to other fragrances, the fragrance has a sweetness and a flower. Such softness can be imparted, and it can be widely used for perfumes, soaps, shampoos, rinses, detergents, cosmetics, sprays, fragrances and the like that require perfume.

Continuation of the front page (72) Inventor Nao Toi, 2-1-3 Bunka, Sumida-ku, Tokyo Kao Corporation Stock Research Institute

Claims (1)

[Claims] 1. The following formula (1): A perfume composition containing 4- (2-methoxyphenyl) -2-methyl-2-butanol represented by: