JP6102547B2 - Novel ethyladamantanediol compound and method for producing the same - Google Patents

Description

  The present invention relates to a novel ethyladamantanediol compound and a method for producing the same.

  Polyester resins synthesized from alicyclic dicarboxylic acids and alicyclic diols are excellent in transparency, heat resistance, weather resistance, gas barrier properties, and optical properties, so they can be used for optical materials, electronic information materials, medical device materials, etc. Can be used.

For example, 1,4-cyclohexanedicarboxylic acid (1,4-CHDA) as alicyclic dicarboxylic acid and 1,4-cyclohexanedimethanol (1,4-CHDM) as alicyclic diol are excellent in biodegradability. Polyester resin (Patent Document 1), conductive polyester (Patent Document 2) with a small amount of released gas, and polyester suitable for medical use are synthesized (Patent Document 3). Further, tricyclo alicyclic dicarboxylic acid [3.3.1.1 ^{3, 7]} decane dicarboxylic acid, optically using a tricyclo [3.3.1.1 ^{3, 7]} decane diol alicyclic diols different A polyester resin having a small isotropic property and excellent moldability is synthesized (Patent Document 4).

JP 2000-290356 A JP 2004-124022 A JP 2005-298555 A Japanese Patent No. 3862538

  An object of the present invention is to provide a novel ethyladamantanediol compound having an alicyclic structure useful as a raw material for producing various industrial chemical raw materials, optical functional materials and electronic functional materials, and a method for producing the same.

As a result of studying a method for producing a novel alicyclic diol compound represented by the formula (1) from 1-ethyladamantane represented by the formula (4), the present inventors have found that hydrogen fluoride (hereinafter referred to as HF). And 1-ethyladamantane represented by formula (4) and carbon monoxide in the presence of boron trifluoride (hereinafter also referred to as BF ₃ ), and then represented by formula (3). Ethyl adamantane dicarboxylic acid fluoride is reacted with an alcohol to obtain an ethyl adamantane dicarboxylic acid ester compound represented by the formula (2), and then the ethyl adamantane dicarboxylic acid ester compound represented by the formula (2) is reduced to give a formula ( It was found that the novel ethyladamantanediol compound represented by 1) can be produced.
The present invention has been completed based on such findings.

（式中Ｒは炭素数1〜４のアルキル基、m、nは0又は1の数値である。）

(In the formula, R is an alkyl group having 1 to 4 carbon atoms, and m and n are values of 0 or 1.)

That is, the present invention is as follows.
[1] An ethyladamantanediol compound represented by the following formula (1).

（式中m、nは0又は1の数値である。）

(In the formula, m and n are numerical values of 0 or 1.)

[2] In the presence of hydrogen fluoride and boron trifluoride, 1-ethyladamantane represented by the chemical formula (4) is reacted with carbon monoxide, and then the ethyladamantanedicarboxylic acid represented by the chemical formula (3) thus obtained is reacted. An acid fluoride is reacted with an alcohol to obtain an ethyladamantane dicarboxylic acid ester compound represented by the chemical formula (2), and then the ethyladamantane dicarboxylic acid ester compound represented by the chemical formula (2) is reduced to obtain a chemical formula (1) A method for producing an ethyladamantanediol compound, comprising producing the ethyladamantanediol compound represented.

（式中Ｒは炭素数1〜４のアルキル基、m、nは0又は1の数値である。）

(In the formula, R is an alkyl group having 1 to 4 carbon atoms, and m and n are values of 0 or 1.)

  When the novel ethyladamantanediol compound represented by the formula (1) of the present invention is used as a raw material for a polyester resin, the material exhibits excellent optical properties and heat resistance.

The result of the ¹³ C-NMR measurement by the inverse gate decoupling method of the main component obtained in Example 1 is shown. The result of DEPT135 degree-NMR measurement of the main component obtained in Example 1 is shown. The result of DEPT90 degree-NMR measurement of the main component obtained in Example 1 is shown. The result of the HSQC-NMR measurement of the main component obtained in Example 1 is shown. It is an enlarged view of the measurement result of 0.77-1.51 ppm part in FIG. The result of the HMBC-NMR measurement of the main component obtained in Example 1 is shown. It is an enlarged view of the measurement result of 0.50 to 1.70 ppm part in FIG. The result of the COSY-NMR measurement of the main component obtained in Example 1 is shown.

  Hereinafter, a mode for carrying out the present invention (hereinafter simply referred to as “the present embodiment”) will be described in detail. The following embodiments are examples for explaining the present invention, and are not intended to limit the present invention to the following contents. The present invention can be implemented with appropriate modifications within the scope of the gist thereof.

The novel ethyladamantanediol compound of the present embodiment is a compound represented by the above formula (1).
In addition, the method for producing the novel ethyladamantanediol compound of the present embodiment is as follows:
(A) A step of reacting 1-ethyladamantane represented by the above formula (4) with carbon monoxide in the presence of HF and BF ₃ to obtain ethyladamantane dicarboxylic acid fluoride represented by the formula (3) ( Hereinafter, it may be abbreviated as “carbonylation step”),
(B) Next, a step of reacting with an alcohol to obtain an ethyladamantane dicarboxylic acid ester compound represented by the formula (2) (hereinafter sometimes abbreviated as “esterification step”), and (c) the obtained ethyl It comprises a step of reducing the adamantane dicarboxylic acid ester compound to obtain ethyl adamantane alcohol represented by the formula (1) (hereinafter sometimes abbreviated as “reduction step”).

<(A) Carbonylation step>
The carbonylation reaction of 1-ethyladamantane is carried out under pressure of carbon monoxide in the presence of HF and BF ₃ . Thereby, the ethyladamantane carbonyl compound (ethyladamantane dicarboxylic acid fluoride) represented by the formula (3) is obtained together with various by-products (including other isomers).

（式中m、nは0又は1の数値である。）

(In the formula, m and n are numerical values of 0 or 1.)

[Carbon monoxide]
Carbon monoxide used in the carbonylation step of the present embodiment may contain an inert gas such as nitrogen or methane, but the carbon monoxide partial pressure is 0.5 to 5 MPa, preferably 1 to 4 MPa. Implement in scope. If the carbon monoxide partial pressure is higher than 0.5 MPa, the carbonylation reaction proceeds sufficiently, and side reactions such as disproportionation and polymerization do not occur at the same time, and the target product, ethyladamantane dicarboxylic acid fluoride, is obtained in high yield. Can be obtained. The carbon monoxide partial pressure is preferably 5 MPa or less from the viewpoint of equipment load.

[Hydrogen fluoride]
Since HF used in the carbonylation step is a solvent for the reaction, a catalyst, and a secondary material, a substantially anhydrous one is used. The amount of HF to be used is 10 to 60 mol times, preferably 15 to 50 mol times with respect to 1-ethyladamantane as a raw material. If the molar ratio of HF is 10 mol times or more, the carbonylation reaction proceeds efficiently, side reactions such as disproportionation and polymerization can be suppressed, and the target product, ethyladamantane dicarboxylic acid fluoride, is obtained in high yield. be able to. In addition, from the viewpoint of raw material cost and productivity, it is preferable to use 60 mol times or less of HF.

[Boron trifluoride]
The amount of BF ₃ used is in the range of 0.3 to 2.0 mol times, preferably 0.5 to 1.5 mol times relative to the raw material 1-ethyladamantane. If the molar ratio of BF ₃ is 0.3 mol times or more, the carbonylation reaction proceeds efficiently. Moreover, if the molar ratio of BF ₃ is 2.0 mol times or less, the BF 3 partial pressure becomes excessive and the carbon monoxide partial pressure is not suppressed, so that a good yield is obtained.

[Reaction conditions]
The type of the carbonylation reaction is not particularly limited, and any method such as a batch system, a semi-continuous system, or a continuous system may be used.

  The reaction temperature of the carbonylation reaction is 45 ° C to 90 ° C, preferably 60 ° C to 80 ° C. The carbonylation reaction proceeds at a reaction temperature of 45 ° C. or higher. However, since polymerization occurs at 80 ° C. or higher, it is preferably performed at around 70 ° C. from the viewpoint of selectivity and reaction rate.

<(B) Esterification step>
The ethyladamantane dicarboxylic acid fluoride reaction solution produced by the carbonylation reaction is reacted with an alcohol having 1 to 4 carbon atoms to obtain an ethyladamantane dicarboxylic acid ester compound. In this case, a method of adding a predetermined amount of alcohol to the ethyladamantane dicarboxylic acid fluoride reaction liquid is preferable from the viewpoint of the corrosiveness of the reaction apparatus.
Moreover, the ethyladamantane dicarboxylic acid fluoride reaction solution produced by the carbonylation reaction is purified by a conventional method such as distillation after distilling off excess HF instead of the esterification step, and remains as acid fluoride. It can also be used as a raw material for the subsequent reduction step. (II) After distilling off excess HF, hydrolysis is performed to obtain the corresponding carboxylic acid, and the carboxylic acid is purified by a conventional method such as distillation. It can also be used as a raw material for the subsequent reduction step.

（式中Ｒは炭素数1〜４のアルキル基、m、nは0又は1の数値である。）

(In the formula, R is an alkyl group having 1 to 4 carbon atoms, and m and n are values of 0 or 1.)

  Specific alcohols used in the esterification step include methanol, ethanol, n-propanol, i-propanol, n-butyl alcohol, i-butyl alcohol, and t-butyl alcohol. Of these, methanol or ethanol is preferred from the viewpoint of reactivity.

  The usage-amount of alcohol is 1.0-2.5 mol times with respect to the raw material 1-ethyladamantane of a carbonylation process, Preferably it is 1.5-2.2 mol times. If the molar ratio of alcohol is 1.0 mol times or more, it is preferable because the remaining amount of unreacted fluoride is small and the device corrosion in the subsequent process is small. From the viewpoint of suppression, 2.5 mole times or less is preferable.

  The reaction temperature in the esterification step is −40 ° C. or higher and 20 ° C. or lower from the viewpoint of inhibiting decomposition of the ethyladamantane dicarboxylic acid ester compound represented by the chemical formula (2). By setting the reaction temperature to −40 ° C. or higher, the esterification rate can be increased and the yield can be improved. Moreover, by making it 20 degrees C or less, while suppressing decomposition | disassembly of ester, the byproduct of water by the dehydration reaction of alcohol can be suppressed.

  HF is distilled off from the reaction solution containing the obtained ethyladamantane dicarboxylic acid ester compound represented by the formula (2), and then purified by a conventional method such as distillation.

<(C) Reduction step>
For the reduction of the ethyladamantane dicarboxylic acid ester compound represented by the formula (2) obtained in the esterification step, any method can be used as long as it is usually used for reducing a carbonyl compound to an alcohol, and there is no particular limitation. . For example, any of hydride reduction, reduction with metal and metal salt, catalytic hydrogenation, etc. described in 5th edition, Laboratory Chemistry Vol. 14 (Maruzen Co., Ltd.), pages 11 to 27 can be used. Reduction by crystallization is preferred.

（式中Ｒは炭素数1〜４のアルキル基、m、nは0又は1の数値である。）

(In the formula, R is an alkyl group having 1 to 4 carbon atoms, and m and n are values of 0 or 1.)

[Hydrogenation catalyst]
The catalyst used for the catalytic hydrogenation of the ethyladamantane dicarboxylic acid ester compound is not particularly limited as long as it is a normal catalyst used for the hydrogenation of carbonyl compounds, but at least one selected from metals in Groups 8 to 11 of the periodic table is used. The containing catalyst is preferred.

  Specific examples include a catalytic hydrogenation catalyst containing at least one selected from iron, cobalt, nickel, copper, ruthenium, rhodium, palladium, silver, osmium, iridium, platinum and gold.

  The catalytic hydrogenation catalyst may be a solid catalyst or a homogeneous catalyst, but is preferably a solid catalyst from the viewpoint of separability from the reactants. Examples of the solid catalyst include a non-supported metal catalyst and a supported metal catalyst.

  The unsupported metal catalyst is preferably a Raney catalyst such as Raney nickel, Raney cobalt, Raney copper, or an oxide or colloid catalyst such as platinum, palladium, rhodium, or ruthenium.

  Supported metal catalysts include magnesia, zirconia, ceria, diatomaceous earth, activated carbon, alumina, silica, zeolite, or titania on iron, cobalt, nickel, copper, ruthenium, rhodium, palladium, silver, osmium, iridium, platinum Examples include those in which at least one kind of gold is supported or mixed, copper-chromium catalyst (Adkins catalyst), supported copper catalyst such as copper-zinc catalyst or copper-iron, supported Pt / C, Pt / alumina, etc. A platinum catalyst, a supported palladium catalyst such as Pd / C or Pd / alumina, a supported ruthenium catalyst such as Ru / C or Ru / alumina, or a supported rhodium catalyst such as Rh / C or Rh / alumina is preferred. Among these, the use of a catalyst containing at least one selected from nickel and copper is more preferable in terms of reaction activity.

  The amount of the catalytic hydrogenation catalyst used varies depending on the type of the catalyst, but it is 1 to 100% by mass, preferably 3 to 30% by mass, based on the ethyladamantane dicarboxylic acid ester compound as the raw material.

[solvent]
Although the reduction process of this embodiment can be performed without a solvent, a solvent may be used.

  As a solvent for the reduction process of this embodiment, organic acids such as water, formic acid and acetic acid, aromatic compounds such as benzene, o-dichlorobenzene, toluene and xylene, hydrocarbons such as hexane, heptane and cyclohexane, methanol and ethanol , Alcohols such as isopropyl alcohol, t-butyl alcohol, ethylene glycol and diethylene glycol, ethers such as dioxane, tetrahydrofuran, dimethoxyethane and diglyme, and mixtures thereof. Among these, solvent-free, aromatic compounds such as benzene, o-dichlorobenzene, toluene, xylene, hydrocarbons such as hexane, heptane, cyclohexane, methanol, ethanol, isopropyl alcohol, t-butyl alcohol, ethylene glycol, It is preferable to use alcohols such as diethylene glycol, ethers such as dioxane, tetrahydrofuran, dimethoxyethane, diglyme, or a mixture thereof.

  The amount of the solvent used in the reduction step of the present invention is usually in the range of 0 to 30 times the mass of the ethyladamantane dicarboxylic acid ester compound represented by the formula (2) obtained in the esterification step. However, 0 to 20 times by mass is preferable.

[Reaction conditions]
The hydrogen pressure in the reduction step of the present embodiment is preferably as high as possible from the viewpoint of moving the reaction equilibrium to the alcohol side, but is preferably 1 to 30 MPa, more preferably 5 to 25 MPa in consideration of equipment costs. -20 MPa is more preferable.

  The reaction temperature in the reduction step of the present embodiment is preferably 100 ° C. or higher, more preferably 150 ° C. or higher, from the viewpoint of obtaining a sufficient reaction rate. Moreover, 300 degreeC or less is preferable and 280 degrees C or less is more preferable from a viewpoint which suppresses transesterification with the ethyladamantanediol produced | generated and the ethyladamantane dicarboxylic acid ester compound represented by Formula (2).

  The form of the reduction process of this embodiment is not particularly limited. Even when the catalytic hydrogenation is performed, the catalytic hydrogenation reaction is not particularly limited as long as the catalytic hydrogenation reaction is possible. For example, a suspension bed reactor in which a catalyst is fluidized with a fluid to perform a catalytic hydrogenation reaction, a fixed bed reactor in which a catalytic hydrogenation reaction is performed by filling and fixing the catalyst and supplying a fluid can be used.

  C1-C4 alcohol byproduces during reaction. The reaction can be carried out in the presence of them, but can also be carried out while removing them continuously or intermittently during the reaction.

After separating the hydrogenation catalyst from the ethyladamantanediol product thus obtained and purifying it according to a conventional method such as distillation or recrystallization, the novel ethyladamantanediol represented by the high purity formula (1) is obtained. Can be obtained.

  EXAMPLES Hereinafter, although an Example demonstrates this invention concretely, this invention is not limited at all by these Examples. In the following, “%” means mass% unless otherwise specified.

<Analysis methods and conditions>
[Gas chromatography analysis conditions]
For gas chromatography, GC-17A manufactured by Shimadzu Corporation and HR-1 manufactured by ULBON (0.32 mmφ × 25 m × 0.50 μm) were used as capillary columns. The temperature was raised from 100 ° C. to 300 ° C. at a rate of 5 ° C./min.

[Conversion rate of ethyl adamantane]
By gas chromatography analysis, the weight ratio (wt%) of the starting ethyl adamantane was determined by the internal standard method, and the conversion rate was calculated by the following formula.
Conversion (mol%) = 100− {Remaining amount of raw material / Amount of raw material charged × 100}
[Ethyl adamantane dicarboxylic acid ester compound yield, ester compound composition ratio]
By gas chromatography analysis, the weight ratio (wt%) of several kinds of ethyladamantane dicarboxylic acid ester compounds (hereinafter sometimes abbreviated as “di-isomers”), which are products of the esterification reaction, is determined by an internal standard method. The total yield and the production ratio of each dimer were calculated by the following formula. As will be described later, the di-form has three kinds of components with a relatively large production amount, which are referred to as di-form [A], di-form [B] and di-form [C], respectively. Ingredients other than seeds shall be other di forms.
{Di-isomer total yield (mol%)} = {Di-isomer [A] acquisition amount / 280.4 + Di-isomer [B] acquisition amount / 294.4 + Di-isomer [C] acquisition amount / 308.4 + Other di-isomers Acquired amount / 294.4} / {raw material charge / 164.3} × 100
{Di-body composition ratio (%)} = {each di-body composition (di-body [A], di-body [B], di-body [C], other di-body) (%)} / {di-body total composition ( %)} × 100

[Ethyl adamantanediol compound yield]
The area ratio (GC%) of several kinds of ethyladamantanediol compounds as products is obtained by gas chromatography analysis, and the yield of 3-ethyl-5- (hydroxymethyl) adamantan-1-yl) ethanol is determined by an internal standard method. Calculated.

[GC-MS]
Waters GC-MS equipment GCT Premier

[NMR]
Apparatus: Bruker Avance 600II (600 MHz-NMR)
Mode: Proton, Carbon, Carbon (Inverse gate decoupling method), DEPT 90 °, 135 °, HSQC, HMBC, COSY
Solvent: CDCl3 (deuterated chloroform)
Internal standard: Tetramethylsilane

<Example 1>
Production of ethyladamantanediol compounds. ((A) carbonylation step, (b) esterification step, and (c) reduction step)

（式中m、nは0又は1の数値である。）

(In the formula, m and n are numerical values of 0 or 1.)

[Carbonylation step]
A stainless-steel autoclave with an internal volume of 500 ml, equipped with a nack drive agitator, three inlet nozzles at the top, and one extraction nozzle at the bottom, which can suppress the internal temperature by the jacket, is cooled with 1-ethyladamantane (Shanghai Hiroyasu Fine Chemical) Co., Ltd.) 33.0 g (0.20 mol), anhydrous HF 201.0 g (10.04 mol), BF ₃ 10.2 g (0.15 mol) were charged, the contents were stirred, and the liquid temperature was raised to 70 ° C. Thereafter, the pressure was increased to 3 MPa with carbon monoxide. Thereafter, the carbonylation reaction was carried out by maintaining the pressure at 3 MPa and the liquid temperature at 70 ° C. for 6 hours.

[Esterification process]
Subsequently, after the reaction temperature was cooled to 5 ° C., 12.9 g (0.40 mol) of methanol was supplied from the top of the autoclave, and esterification was performed for 1 hour with stirring.
The reaction solution was extracted from the bottom of the autoclave into ice water, and the oil phase and the aqueous phase were separated. The oil phase was then washed twice with 100 ml of 2% aqueous sodium hydroxide solution and twice with 100 ml of distilled water, and dehydrated with 10 g of anhydrous sodium sulfate. .
The obtained reaction liquid was subjected to internal standard analysis by gas chromatography. As a result, the conversion rate was 100 mol%, the di-isomer total yield was 55.1 mol% (based on 1-ethyladamantane), and di-form [A], di-form. [B], di-form [C], and di-form composition ratio of other di-forms were 13.2%, 60.9%, 12.5%, and 13.4%, respectively.

[Isolation and purification of esterification reaction product]
After removing low boiling substances from the obtained liquid using an evaporator, rectification was performed using a rectification column having 50 theoretical plates (distillation temperature: 159 ° C., vacuum degree: 2 torr). The purity of di-form [A], di-form [B], di-form [C], and other di-forms was determined to be 3.5%, 83.5%, 3.8%, and 9.2%, respectively, by graphic analysis. Of 28.0 g (distillation yield 54.1 mol%, based on esterification reaction solution). The molecular weight of the main component di-form [B] measured by GC-MS was 294. Considering the result of identification of the product of the reduction step described later, the di-form [B] was methyl-3-ethyl- It is thought to be 5- (2-methoxy-2-oxoethyl) adamantane-1-carboxylate.

[Reduction process]
Preparation of 3-ethyl-5- (hydroxymethyl) adamantan-1-ylethanol.

In a stainless steel autoclave, 2.7 g of a copper-zinc catalyst (manufactured by JGC Catalysts & Chemicals) supported on alumina and an ester mixture (methyl-3-ethyl-5- (2-methoxy-2-oxoethyl) obtained from the main fraction part Adamantane-1-carboxylate purity 83.5%, including other di-isomers 16.5%) 27.0 g was added and stirred at 250 ° C. for 10 hours under a hydrogen pressure of 15 MPa while flowing hydrogen without solvent. The reduction reaction was performed.
The reaction solution was filtered to remove the catalyst, and 20 products (mixtures) containing 84.3% of 3-ethyl-5- (hydroxymethyl) adamantan-1-ylethanol and 14.7% of other ethyladamantanediol compounds were obtained. Yield of 95.6 mol% of (3-ethyl-5- (hydroxymethyl) adamantan-1-ylethanol produced, 0.7 g of methyl-3-ethyl-5- (2-methoxy-2-oxoethyl) adamantane-1 -Carboxylate basis).

[Isolation and purification of reduction reaction product]
When the obtained liquid was subjected to rectification using a single distillation column (distillation temperature: 157 ° C., vacuum degree: 4 torr), 3-ethyl-5- (hydroxymethyl) adamantane- was obtained as a main fraction by gas chromatography analysis. 13.2 g of a product containing 14.4% of 1-ylethanol and 15.6% of other ethyladamantanediol compounds (distillation yield: 64.0 mol%, 3-ethyl-5- (hydroxy Methyl) adamantane-1-ylethanol standard).

<Identification of product>
As a result of performing GC-MS analysis on the product obtained by isolation and purification of the reduction reaction product of Example 1, the molecular weight was 238.
Further, using the NMR apparatus, 1H-NMR measurement, 13C-NMR measurement, 13C-NMR measurement (Inverse gate decoupling method), dept90-NMR measurement, dept135-NMR measurement, HSQC-NMR measurement, HMBC-NMR measurement, COSY-NMR measurement was performed.
The results of 1H-NMR measurement and 13C-NMR measurement are shown below, and NMR measurement by inverse gate decoupling method, depth 135 °, 90 ° -NMR measurement, HSQC-NMR measurement, HMBC-NMR measurement, COSY-NMR measurement and results are shown. Shown in FIGS.

[NMR measurement result of the product obtained in Example 1]
1H-NMR (600 MHz, CDCl3, TMS, ppm) [delta]: 0.792 (t, 3H), 1.139 to 1.202 (m, 8H), 1.256 to 1.456 (m, 10H), 2 118 (m, 1H), 3.248 (m, 2H), 3.723 (m, 2H)
13C-NMR (600 MHz, CDCl 3, TMS, ppm) δ: 7.07, 28.96, 32.94, 33.30, 35.97, 36.02, 38.21, 40.95, 41.90, 42.91, 43.88, 46.57, 46.95, 58.83, 73.44

FIG. 1 shows the result of ¹³ C-NMR measurement by the inverse gate decoupling method. From FIG. 1 it can be seen that the two methanol carbons are not equivalent. FIG. 2 shows the results of DEPT135 ° -NMR measurement. Secondary carbon atoms # 1, # 2, # 3, # 4, # 5, # 6, # 7, # 8, # 9 and # 10 are detected downward, and The peak disappearance of No. 11, No. 12 and No. 13 is known. FIG. 3 shows the results of DEPT 90 ° -NMR measurement. It can be seen that the peak No. 14 which is a tertiary carbon atom is strongly detected. 4 and 5 show the results of HSQC-NMR measurement (FIG. 5 is an enlarged view of the measurement results in the 0.77 to 1.51 ppm portion in FIG. 4). From FIG. 4 and FIG. 5, it is grasped about the hydrogen atom bonded to each carbon atom. 6 and 7 show the results of HMBC-NMR measurement (FIG. 7 is an enlarged view of the measurement results at 0.50 to 1.70 ppm in FIG. 6). From FIG. 6 and FIG. 7, it is understood about hydrogen atoms that are two bonds away from each carbon atom. FIG. 8 shows the results of COSY-NMR measurement. The hydrogen atoms of adjacent carbon atoms are grasped.
Judging comprehensively from these measurement results, the main component was identified as 3-ethyl-5- (hydroxymethyl) adamantan-1-ylethanol.

  The novel ethyladamantanediol compound obtained in the present invention is useful as a raw material for producing various industrial chemical raw materials, optical functional materials and electronic functional materials.

Claims (2)

An ethyladamantanediol compound having a chemical structural formula represented by formula (1).

(In the formula, m and n are numerical values of 0 or 1.) In the presence of hydrogen fluoride and boron trifluoride, 1-ethyladamantane represented by the formula (4) is reacted with carbon monoxide, and then the obtained ethyladamantane dicarboxylic acid fluoride represented by the formula (3) is reacted. After reacting with alcohol to obtain an ethyladamantane dicarboxylic acid ester compound represented by the formula (2), the ethyladamantane dicarboxylic acid ester compound represented by the formula (2) is reduced to be represented by the formula (1). A method for producing an ethyladamantanediol compound, comprising producing an ethyladamantanediol compound.

(In the formula, R is an alkyl group having 1 to 4 carbon atoms, and m and n are values of 0 or 1.)

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