JP2000103754A - Production of aromatic-based carbinols - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject compound at a high yield by reacting Grignard's reagent to a compound obtained by reacting hydrogen with acetone and an aromatic aldehyde in the presence of a basic material and a hydrogen addition catalyst. SOLUTION: A compound of the formula, e.g. dimethylphenethyl carbinol is obtained by reacting (E) a Grignard's reagent (e.g. methylmagnesium chloride) expressed by the formula: RMgX (R is a hydrocarbon; X is a halogen) with (D) a compound of the formula: Ar-CH2-CH2-CO-CH3 obtained by reacting hydrogen with acetone and (C) on aromatic aldehyde (e.g. benzaldehyde) of the formula: Ar-CHO (Ar is an aromatic compound selected from phenyl, naphthyl and furyl) in the presence of (A) a basic material (e.g. sodium hydroxide) and (B) a hydrogen addition catalyst (e.g. palladium carbon). Preferably, a using amount of the component E is 0.5-2 mol to 1 mol of the component D.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention has a soft green and floral fragrance reminiscent of lily and hyacinth, and is represented by dimethylphenethylcarbinol, methylethylphenethylcarbinol and the like which are used in floral-based compounded fragrances. The following equation (1)

[0002]

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[Wherein, Ar represents an aromatic group selected from the group consisting of a phenyl group, a naphthyl group and a furyl group.
However, the aromatic group may be an alkyl group, an alkoxy group which may be substituted by a fluorine atom, or a compound represented by the formula -O-W-O
-(Wherein, W represents an alkylene group). And a method for producing an aromatic carbinol represented by the formula:

[0004]

2. Description of the Related Art As a method for producing an aromatic carbinol represented by the above formula (1), a method of reacting benzylacetone with a methyl Grignard reagent is known, for example, taking dimethylphenethyl carbinol as an example. (Osamu Okuda, "Perfection Chemistry Directory II", published by Hirokawa Shoten, p. 673). Benzyl acetone used as a raw material in this production method is produced by condensing benzaldehyde and acetone with an aqueous solution of sodium hydroxide to produce benzalacetone, and further hydrogenating the obtained benzalacetone. It can be manufactured (see Okuda Osamu, "Perfumery Chemical Directory II", published by Hirokawa Shoten, pp. 1003 to 1004). As another method for producing dimethylphenethyl carbinol, there is known a method in which a phenethyl Grignard reagent obtained by halogenating a hydroxyl group of phenethyl alcohol and reacting with magnesium is reacted with acetone (Okuda Osamu; Chemical Directory II ”, published by Hirokawa Shoten, 673
Page).

[0005]

As described above, dimethylphenethyl carbinol can be produced in three steps by using benzaldehyde and acetone, which are industrially easily available, as raw materials and further reacting with a methyl Grignard reagent. However, in the first step, condensation of benzaldehyde and acetone, it is difficult to obtain benzalacetone selectively and in good yield. In the same condensation, it is said that by using a large amount of acetone, the generation of by-products can be suppressed.However, the use of a large amount of acetone reduces the volumetric efficiency of the reaction and reduces the volume of acetone. This leads to an increase in cost and is not advantageous for industrial implementation.

On the other hand, a method of reacting phenethyl Grignard reagent with acetone is based on phenethyl alcohol.
This is a production method requiring a step, and the production cost of dimethylphenethylcarbinol increases because phenethyl alcohol is relatively expensive. As described above, several methods for producing dimethylphenethyl carbinol are known, but there is a point that it is desirable to improve the method for industrial implementation. From an industrial point of view, reducing the number of manufacturing steps as much as possible is advantageous in terms of operability, equipment, process control, etc., and contributes to a reduction in manufacturing costs.

Accordingly, an object of the present invention is to provide a method for industrially advantageously producing an aromatic carbinol represented by the above formula (1) represented by dimethylphenethyl carbinol. I do.

[0008]

According to the present invention, the above objects have been achieved in the presence of a basic substance and a hydrogenation catalyst in the presence of hydrogen, acetone and the formula (2) Ar-CHO (2) Ar represents an aromatic group selected from the group consisting of a phenyl group, a naphthyl group and a furyl group. However, the aromatic group is an alkyl group, an alkoxy group which may be substituted by a fluorine atom, or a compound represented by the formula -OWO- (wherein W is
Represents an alkylene group). To produce a compound represented by the formula (3) Ar-CH ₂ —CH ₂ —CO—CH ₃ (3) (where Ar is as defined above) And the obtained compound represented by the formula (3)
Formula (1) comprising reacting a Grignard reagent represented by the formula (4): RMgX (4), wherein R represents a hydrocarbon group and X represents a halogen atom.

[0009]

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The problem is solved by providing a method for producing an aromatic carbinol represented by the formula: wherein Ar and R are as defined above.

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail.
In the present invention, first, a compound represented by the above formula (3) is produced by reacting hydrogen, acetone and an aromatic aldehyde represented by the above formula (2) in the presence of a basic substance and a hydrogenation catalyst. I do.

In the above formula (2), examples of the alkyl group which the aromatic group represented by Ar may have and which may be substituted by a fluorine atom include, for example, a methyl group, an ethyl group and an isopropyl group , T-butyl group, trifluoromethyl group and the like. Examples of the alkoxy group which the aromatic group represented by Ar may have include a methoxy group, an ethoxy group, and a propoxy group. Furthermore, in the group represented by the formula —O—W—O— (W represents an alkylene group) which the aromatic group represented by Ar may have, W is, for example, a methylene group or an ethylene group , A propylene group, a 1,1-dimethylmethylene group and the like. Among these, as a substituent which the aromatic group represented by Ar may have,
A methoxy group is preferred. For the position of the substituent,
It may be in any of ortho, meta and para positions relative to the aldehyde group (CHO), and is not particularly limited. Also,
There is no particular limitation on the number of substituents as long as it is within an allowable range.

Specific examples of the aromatic aldehyde represented by the formula (2) include, for example, benzaldehyde, o-tolylaldehyde, p-tolylaldehyde, 2,4-dimethylbenzaldehyde, 2-methyl-5-isopropylbenzaldehyde (P-cymene-2-aldehyde), cuminaldehyde, 4- (trifluoromethyl) benzaldehyde, p-anisaldehyde, 2,4-dimethoxybenzaldehyde, 3,4-dimethoxybenzaldehyde (methylvanillin), 5-methoxy-3 , 4-Methylenedioxybenzaldehyde, 1-naphthaldehyde, 2
-Naphthaldehyde, 6-methoxy-2-naphthaldehyde, furfural and the like.

The ratio of the aromatic aldehyde represented by the formula (2) to acetone is not particularly limited, but the selection of the compound represented by the formula (3) based on the more expensive aromatic aldehyde is preferred. Increasing the rate is industrially advantageous. Therefore, the amount of acetone is usually 0.9 to 5 mol, preferably 1 to 3 mol, more preferably 1.05 to 1.5 mol, per 1 mol of the aromatic aldehyde represented by the formula (2). Used in.

The basic substance used in the present invention includes, for example, hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; hydroxides of alkaline earth metals such as barium hydroxide and calcium hydroxide. Carbonates of alkali metals such as potassium carbonate; and amines such as 1,5-diazabicyclo [5.4.0] undecene-5 (DBU) and piperidine. One of these may be used, or a mixture of two or more may be used.

Although the basic substance can be used as it is, it can also be used as an aqueous solution. In the present invention, among the above basic substances, it is preferable to use an alkali metal hydroxide or an alkaline earth metal hydroxide, and the form of use is usually a 0.5 to 50% by weight aqueous solution, Preferably, it is an aqueous solution of 1 to 30% by weight.

The amount of the basic substance used is usually from 0.005 to 1 mol per mol of the aromatic aldehyde represented by the formula (2).
The amount is 0.3 mol, but from the viewpoint of the reaction rate and the production cost, it is preferably 0.01 to 0.1 mol based on 1 mol of the aromatic aldehyde represented by the formula (2).

As the hydrogenation catalyst used in the present invention, catalysts generally used for catalytic hydrogenation reactions, in particular, carbon-containing α, β-unsaturated carbonyl compounds
A catalyst used for selectively hydrogenating a carbon double bond can be used, and examples thereof include a catalyst containing palladium, rhodium, nickel, platinum or the like as an active component.

The form of the hydrogenation catalyst may be any of a metal itself; a metal oxide or an alloy with another metal; and a catalyst supported on a carrier such as activated carbon, alumina, silica gel, or diatomaceous earth. Among these, palladium carbon, palladium alumina, Raney nickel, platinum carbon and the like are preferable, and palladium carbon, palladium alumina and the like are more preferable.

The amount of the hydrogenation catalyst used is usually 0.001 part by weight based on 1 part by weight of the aromatic aldehyde represented by the formula (2).
0.05 to 0.1 parts by weight, and from the viewpoint of the reaction rate and the production cost of the compound represented by the formula (3), 0.001 to 1 part by weight of the aromatic aldehyde represented by the formula (2).
Preferably, the amount is 0.03 parts by weight.

In the reaction for producing the compound represented by the formula (3), use of a solvent is not always necessary, but a solvent may be used as long as the reaction is not adversely affected. Usable solvents include, for example, ethers such as tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether and dibutyl ether;
Hexane, heptane, octane, benzene, toluene,
Hydrocarbons such as xylene; water and the like.

Specific examples of the reaction for producing the compound represented by the formula (3) include, for example, acetone and an aromatic aldehyde represented by the formula (2) in a predetermined reaction temperature range and under a hydrogen atmosphere. An example is an operation of mixing a kind, a basic substance, and a hydrogenation catalyst by a general operation using a general-purpose device. In this case, there is no particular limitation on the mixing order and mixing speed of each component to be subjected to the reaction, and all components to be subjected to the reaction, that is, acetone, aromatic aldehydes represented by the formula (2), basic substance, and hydrogenation The catalyst may be mixed and reacted at once,
One or two of acetone, the aromatic aldehyde represented by the formula (2) and the basic substance may be charged into a reaction vessel together with a hydrogenation catalyst, and the reaction may be carried out while adding the remaining components to the reaction vessel. . In the latter case, the components to be added may be continuously added into the reaction vessel,
Moreover, you may add intermittently or sequentially in several times. In particular, as a method for mixing each component, a basic substance and a compound represented by the formula (2) are added to a suspension obtained by suspending a hydrogenation catalyst in acetone.
The reaction is carried out while adding the aromatic aldehyde represented by the above, or the remaining basic substance is added to a liquid obtained by mixing a part or all of the basic substance in a suspension in which the hydrogenation catalyst is suspended in acetone. And the aromatic aldehydes represented by the formula (2).

The reaction temperature is usually in the range of 20 to 180 ° C., but from the viewpoint of making the reaction rate practical and increasing the selectivity to the desired compound represented by the formula (3), The temperature is preferably in the range of 40 to 140 ° C.

The time required for the reaction depends on the type, concentration and reaction temperature of the basic substance used, but as described above, the basic substance and the formula ( The reaction is carried out while adding the aromatic aldehydes shown in 2), or a solution obtained by mixing a part or all of a basic substance in a suspension in which a hydrogenation catalyst is suspended in acetone is added to the remaining solution. When the reaction is performed while adding the basic substance and the aromatic aldehyde represented by the formula (2), the time required for adding the basic substance and the aromatic aldehyde represented by the formula (2) is usually 0. 0.5 to 10 hours, and 0 to 20 hours as an additional time after completion of the addition.

During the addition of the basic substance and the aromatic aldehyde represented by the formula (2) and during the driving of the reaction,
It is desirable to sufficiently stir the reaction mixture.

In the present invention, hydrogen may be brought into contact with the surface of a mixture of an aromatic aldehyde represented by the formula (2), acetone, a basic substance and a hydrogenation catalyst, and the hydrogen is introduced (bubbled) into the mixture. ).

The pressure of hydrogen in the reaction system is usually from 1 to 100.
The pressure is in the range of 1 to 10 atm.

After completion of the reaction, the desired compound represented by the formula (3) can be added, if necessary, to an aqueous layer of the reaction mixture obtained by, for example, i) removing the hydrogenation catalyst from the reaction mixture by filtration or centrifugation. And distilling the remaining organic layer, or ii) filtering off the hydrogenation catalyst from the reaction mixture,
The desired compound represented by the formula (3) is extracted from the obtained filtrate with an organic solvent, and the organic solvent is simply distilled off from the obtained organic layer under normal pressure or reduced pressure by a general method. Can be released. In addition, examples of the organic solvent used for the extraction include hydrocarbons such as toluene, benzene, hexane, and cyclohexane; and halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, and dichloroethane.

Next, in the present invention, the compound represented by the formula (3) obtained according to the above method is represented by the formula (4) RMgX (4) (wherein R represents a hydrocarbon group and X represents a halogen atom) With a Grignard reagent represented by
This reaction may be abbreviated as the Grignard reaction according to the present invention) to produce the aromatic carbinols represented by the above formula (1).

Here, in the above formula (4), examples of the hydrocarbon group represented by R include a methyl group, an ethyl group,
n-propyl group, i-propyl group, n-butyl group, i-
Butyl group, sec-butyl group, n-pentyl group, 3-methylbutyl group, n-hexyl group, phenyl group, tolyl group, benzyl group, phenethyl group and the like, among which those having 8 or less carbon atoms Is preferred. Also,
Examples of the halogen atom represented by X include a chlorine atom, a bromine atom, and an iodine atom.

Specific examples of the Grignard reagent represented by the formula (4) include methyl magnesium chloride, methyl magnesium bromide, methyl magnesium iodide, ethyl magnesium chloride, ethyl magnesium bromide, n-butyl magnesium bromide, phenyl magnesium bromide, Benzyl magnesium chloride, phenethyl magnesium chloride and the like can be mentioned. The Grignard reagent represented by the formula (4) can be prepared by reacting a halide such as methyl chloride, methyl bromide, ethyl chloride or benzyl chloride with magnesium metal in a conventional manner. As the Grignard reagent represented by the formula (4), a commercially available reagent may be appropriately used.

The amount of the Grignard reagent represented by the formula (4) is usually 0.5 to 2 mol, preferably 0.8 to 1.5 mol, per 1 mol of the compound represented by the formula (3). is there.

The Grignard reaction according to the present invention generally comprises
It is performed in the presence of a solvent. Possible solvents include:
Examples include ethers such as diethyl ether and tetrahydrofuran. The amount of the solvent to be used is not particularly limited, but is usually 0.5 to 100 times, preferably 1 to 20 times the weight of the compound represented by the formula (3).

The Grignard reaction according to the present invention can be carried out according to the same operation as a usual addition reaction of a Grignard reagent to ketones. As a specific reaction operation, for example, a method in which a compound represented by the formula (3) is added to the Grignard reagent represented by the formula (4) in the above-mentioned solvent.

The Grignard reaction according to the present invention usually comprises-
It is carried out at a temperature of 10 to 80C, preferably at a temperature of 0 to 40C. The Grignard reaction according to the present invention is preferably carried out in an atmosphere of an inert gas such as nitrogen or argon.

After completion of the reaction, the aromatic carbinol represented by the formula (1), which is a product, can be separated and obtained from the reaction mixture according to a conventional method. To give an example, an acid such as dilute sulfuric acid, dilute hydrochloric acid or a saturated aqueous solution of ammonium chloride is added to the reaction mixture to hydrolyze it, and then i) the organic layer is separated or ii) carbonization of toluene, benzene, hexane, cyclohexane or the like. The aromatic carbinols represented by the formula (1) are extracted using hydrogen or a halogenated hydrocarbon such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, etc., and the solvent is extracted from the obtained organic layer or extract. There is a method of removing.

The thus obtained aromatic carbinol represented by the formula (1) can be further increased in purity by a conventional method such as distillation under reduced pressure and silica gel column chromatography.

[0038]

EXAMPLES The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples.

Example 1 (a) Production of benzylacetone from benzaldehyde and acetone 601.9 g (10.38 mol) of acetone was charged into a 5-liter internal stainless steel autoclave equipped with a stirrer, and charged under a nitrogen atmosphere. 2.0 g of palladium carbon (hydrogenation catalyst, water content: about 50%) was added, and the internal temperature of the autoclave was raised to 80 ° C. Thereafter, hydrogen was introduced into the autoclave to adjust the pressure in the autoclave to 7.0 kg / cm ² (gauge pressure, hydrogen partial pressure therein: 4.9 kg / cm ² ), and then to 1005.1 g of benzaldehyde (9.43). Mol) and 377.2 g of a 2% aqueous sodium hydroxide solution (containing 0.19 mol of sodium hydroxide) were each added continuously to the mixture obtained above using a feed pump. The time required for the addition was 6 hours for benzaldehyde and 4 hours for 2% aqueous sodium hydroxide. During the addition, the temperature of the reaction mixture was maintained at 80 ° C., and the amount of hydrogen consumed in the reaction was supplied to the autoclave, and the pressure inside the autoclave was maintained at 7.0 kg / cm ² (gauge pressure). did. After completion of the addition of benzaldehyde, stirring was continued for 1.5 hours while maintaining the temperature of the reaction mixture at 80 ° C. to drive the reaction, followed by cooling to room temperature. Palladium carbon was removed from the resulting reaction mixture by filtration,
1416.0 g of the organic layer was obtained from the filtrate separated into two layers. The obtained organic layer was subjected to gas chromatography [column: G-100 (trade name, manufactured by The Chemicals Inspection Association), column diameter: 1.2 mm, column length: 20 m, column temperature: 70 → 200 ° C. (heating rate) : 5 ° C / min)]. As a result, the unreacted raw material, benzaldehyde, was 5.1.
g, 33.6 g of benzyl alcohol in which the carbonyl group of benzaldehyde was reduced, and 1135.6 g of the target benzyl acetone. The yield of benzylacetone based on benzaldehyde was 81.
4%. Of the organic layers obtained above, 140
By distilling 4.1 g under reduced pressure, the boiling point is 110 to 110 g.
1138.6 g as a fraction at 114 ° C./1.8 mmHg
I got Benzyl acetone was contained in this fraction in 1113.
5g was contained.

(B) Production of dimethylphenethylcarbinol A 664 solution of methylmagnesium chloride in tetrahydrofuran was placed in a three-liter glass three-necked flask equipped with a stirrer, a condenser and a dropping funnel under a nitrogen atmosphere.
ml (concentration: 2.4 mol / l, containing 1.59 mol of methylmagnesium chloride) and 730 ml of tetrahydrofuran, and the liquid temperature was lowered to 5 using an ice bath.
Adjusted to ° C. Thereafter, the fraction having a boiling point of 110 to 114 ° C./1.8 mmHg obtained in the above (a) 220.9 was obtained.
g [containing 216 g (1.46 mol) of benzylacetone] was dropped into the reactor over 3 hours. During the addition of the fraction containing benzylacetone, the temperature of the reaction solution was kept at 10 ° C. or lower using an ice bath. After the addition of benzylacetone, the ice bath was removed and the temperature of the reaction solution was raised to room temperature (about 20 to
(25 ° C.) to drive the reaction. The resulting reaction mixture was slowly poured into 2340 g of cooled 2.5% hydrochloric acid, stirred and allowed to stand, and separated into two upper and lower layers. Separate the organic layer (upper layer) and add 500 g of 0.5% hydrochloric acid.
And washed. The organic layer 1006.
From 0 g, tetrahydrofuran was distilled off under reduced pressure to obtain 228.3 g of crude dimethylphenethylcarbinol. The obtained crude dimethylphenethyl carbinol was subjected to simple evaporation in order to remove high boiling components, and 78-88 ° C /
209.7 g of a fraction having a boiling point of 0.7 mmHg were obtained. Furthermore, by distilling and purifying this fraction under reduced pressure,
183.5 g of dimethylphenethyl carbinol (boiling point:
73.5 ° C / 0.20 mmHg, purity 99.2%). The yield of dimethylphenethylcarbinol after distillation and purification was 76.1% based on benzylacetone.

Example 2 (a) Production of benzylacetone from benzaldehyde and acetone In a 5 liter stainless steel autoclave equipped with a stirrer, 601.9 g (10.38 mol) of acetone and 377 of a 2% aqueous sodium hydroxide solution were added. 0.2 g (0.1
9 mol), and 2.0 g of 5% palladium carbon (hydrogenation catalyst, containing about 50% water) under a nitrogen atmosphere.
, The internal temperature of the autoclave was raised to 80 ° C. Thereafter, hydrogen was introduced into the autoclave to adjust the pressure in the autoclave to 7.0 kg / cm ² (gauge pressure, hydrogen partial pressure therein: 5.2 kg / cm ² ), and then 1005.1 g of benzaldehyde (9.43). Mol) was added continuously to the mixture obtained above using a feed pump. The time required for the addition of benzaldehyde was 6 hours. During the addition of benzaldehyde, the liquid temperature of the reaction mixture was maintained at 80 ° C., and hydrogen consumed in the reaction was supplied to the autoclave, and the pressure in the autoclave was maintained at 7.0 kg / cm ² (gauge pressure). did.
After the end of the benzaldehyde addition, the temperature of the reaction mixture is raised to 8
Stirring was continued for 2 hours while keeping the temperature at 0 ° C. to drive the reaction, followed by cooling to room temperature. Palladium carbon was removed from the obtained reaction mixture by filtration, and 1425.3 g of the organic layer was separated from the filtrate separated into two layers. The obtained organic layer was analyzed by gas chromatography under the same analysis conditions as in Example 1 (a). As a result, 6.6 g of unreacted raw material, benzaldehyde, and 10 g of benzyl alcohol in which the carbonyl group of benzaldehyde was reduced were obtained. 0.3 g and 1221.2 g of the target benzylacetone were found to be contained. The yield of benzylacetone based on benzaldehyde was 87.5%. Of the organic layers obtained above, 1
Distillation of 410.5 g under reduced pressure gives a boiling point of 11
1209. As a fraction of 0 to 114 ° C / 1.8 mmHg.
5 g were obtained. Benzylacetone was 118 in this fraction.
4.6 g was contained.

(B) Production of dimethylphenethyl carbinol The boiling point obtained in the above (a) is 110 to 114 ° C./1.8 m.
220.5 g of mHg fraction (216 g of benzylacetone)
Was used and crude dimethylphenethylcarbinol was obtained in the same manner as in Example 1 (b). The obtained crude dimethylphenethyl carbinol was subjected to removal of high boiling components and purification by distillation under reduced pressure in the same manner as in (b) of Example 1 to give dimethylphenethyl carbinol 1
88.9 g (boiling point: 73.5 ° C./0.20 mmHg, purity 99.1%) were obtained. The yield of dimethylphenethylcarbinol after distillation and purification was 78.2% based on benzylacetone.

Example 3 In Example 1 (b), 797 ml of a tetrahydrofuran solution of ethyl magnesium chloride was used instead of 664 ml of a tetrahydrofuran solution of methyl magnesium chloride.
l (concentration: 2.0 mol / l, containing 1.59 mol of ethylmagnesium chloride) was carried out in the same manner as in Example 1 (b), except that crude methyl ethylphenethyl carbinol 267 was used. 0.5 g was obtained. The obtained crude methyl ethyl phenethyl carbinol was subjected to removal of high boiling components and purification by distillation under reduced pressure in the same manner as in (b) of Example 1 to give 207.7 g of methyl ethyl phenethyl carbinol (boiling point: 129 to 129). 130 ° C / 13mmH
g, purity 99.1%). The yield of methylethylphenethylcarbinol after distillation and purification was 79.2% based on benzylacetone.

Example 4 (a) Preparation of 4-methoxybenzylacetone from p-anisaldehyde and acetone 1005.1 benzaldehyde as in (a) of Example 1.
1282.5 g of p-anisaldehyde (9.
43 mol), and the same operation as in (a) of Example 1 was carried out, except that 4-methoxybenzylacetone 102
8.5 g (yield based on p-anisaldehyde: 80.
2%). The obtained organic layer was distilled under reduced pressure to obtain 995.0 g (purity: 98.2%) of 4-methoxybenzylacetone.

(B) 4- (p-methoxyphenyl) -2-
Preparation of methyl-2-butanol In Example 1 (b), 221.5 g of 4-methoxybenzylacetone (purity: 98.2%, 1.2 mol) obtained in the above (a) was used instead of 216 g of benzylacetone. ) Was performed in the same manner as in Example 1 (b) except that
238.4 g of crude product were obtained. The obtained crude product was subjected to simple evaporation (removal of high-boiling components) and distillation purification under reduced pressure in the same manner as in (b) of Example 1 to give 4- (p-methoxyphenyl) -2-methyl. -2-butanol 184.
1 g (99.0% purity) was obtained. The yield of 4- (p-methoxyphenyl) -2-methyl-2-butanol after purification by distillation was 78.3% based on 4-methoxybenzylacetone.

[0046]

According to the present invention, there is provided a method for industrially and advantageously producing an aromatic carbinol represented by the above formula (1) represented by dimethylphenethyl carbinol.

 ────────────────────────────────────────────────── ─── Continued on the front page (72) Takashi Onishi Inventor Kuraray 2-28 Kurashiki-cho, Nakajo-machi, Kitakanbara-gun, Niigata F-term (reference) 4H006 AA02 AB14 AC12 AC22 AC25 BA02 BA06 BA22 BA29 BA30 BA32 BA51 BB11 BB15 BB25 4H039 CA29 CA60 CB10

Claims (2)

[Claims] 1. In the presence of a basic substance and a hydrogenation catalyst, hydrogen, acetone, and Ar-CHO (2) wherein Ar is selected from the group consisting of a phenyl group, a naphthyl group, and a furyl group. Represents an aromatic group. However, the aromatic group is an alkyl group, an alkoxy group which may be substituted by a fluorine atom, or a compound represented by the formula -OWO- (wherein W is
Represents an alkylene group). To produce a compound represented by the formula (3) Ar-CH ₂ —CH ₂ —CO—CH ₃ (3) (where Ar is as defined above) And the obtained compound represented by the formula (3)
Formula (1) comprises reacting a Grignard reagent represented by the formula (4): RMgX (4) (wherein, R represents a hydrocarbon group and X represents a halogen atom). (Wherein, Ar and R are as defined above). 2. The method according to claim 1, wherein the basic substance is at least one hydroxide selected from the group consisting of an alkali metal hydroxide and an alkaline earth metal hydroxide.