JP2009078976A - Arene-based compound and its production method, and arene-based compound derivative and its production method - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new arene-based compound which can be chemically modified with ease, has a characteristic three-dimensional structure, and whose utilization as a clathrate compound or the like can be expected. <P>SOLUTION: Provided is an arene-based compound prepared by reacting a raw material compound (A) represented by general formula (1) [wherein, X is a 1-10C alkyl group or the like; m is 0 or 1] with a raw material compound (B) represented by general formula (2) [wherein, Y is a monovalent substituent or the like; n is 0 or 1]. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

  The present invention relates to a novel compound (arene compound and arene compound derivative) that can be expected to be used as an inclusion compound and can be functionalized by introduction of a functional group, and a method for producing the same.

  The calixarene compound is generally a cyclic oligomer obtained by condensation of a phenol compound such as phenol and resorcinol with an aldehyde compound. In recent years, calixarene compounds have attracted attention as third inclusion compounds after crown ether and cyclodextrin in the field of host-guest chemistry.

  The calixarene compound usually has many hydroxyl groups in one molecule, is excellent in thermal stability, has a high glass transition temperature and a high melting point, and has a film forming property depending on the structure. It is attracting attention as a functional material. For example, application to an electron beam negative photoresist using p-methylcalix [6] arene hexaacetate (see, for example, Non-Patent Document 1), calix [4] resorcinarene, crosslinking agent, photoacid generator Application to an alkali developing type negative photoresist based thereon (for example, see Non-Patent Document 2) has been reported. In addition, for the purpose of applying calixarene compounds to high-performance photocuring materials, the introduction of radically polymerizable functional groups and cationically polymerizable functional groups, and protection for the application to high-resolution resist materials Synthesis of calixarene derivatives by introduction of a group and evaluation of the photoreaction characteristics have been reported (for example, see Non-Patent Documents 3, 4 and 5). Moreover, the synthesis | combination of the p-alkyl calix [n] arene derivative which has various cationically polymerizable functional groups and examination about the photocationic polymerization are reported (for example, refer nonpatent literature 6).

  Among calixarene compounds, calixresorcinolarene compounds, which are condensates of resorcinol compounds and aldehyde compounds, have been studied for the purpose of inclusion of large guests, and chemical modification of the resorcinol ring A number of derivatives with larger and deeper pores have been synthesized.

For example, when a hydroxyl pair of adjacent resorcinol rings is cross-linked by a covalent bond, a cage-type cavitand having a firmly fixed corn conformation can be obtained. As such a crosslinking method, alkylation using dihalomethane (see Non-Patent Document 7), silylation using dialkyldichlorosilane (see Non-Patent Document 8), and the like have been reported. In addition, examples using derivatives having functional groups such as CHO (see non-patent document 9), OH (see non-patent document 10), CO ₂ R (see non-patent document 11) have been reported as resorcinol compounds. Yes. Furthermore, it has also been reported that a capsule-type calceland can be obtained by linking two or more types of cavitants having appropriate functional groups by S _N 2 reaction (see Non-Patent Document 12). However, these cavitants are difficult to be further chemically modified because no reactive groups remain.

Y. Ochiai, S .; Manako, H .; Yamamoto, T .; Teshima, J .; Fujita, E .; Nomura: J. et al. Photopolymer. Sci. Tech. 13,413 (2000) T.A. Nakayama, M .; Nomura, K .; Haga, M .; Ueda: Bull. Chem. Soc. Jpn. 71, 2979 (1998) T.A. Nishikubo, A .; Kameyama and H.K. Kudo, K, Tsutsui, J. et al. Polym. Sci. Part. Part A, Polym. Chem, 39, 1293 (2002) T.A. Nishikubo, A .; Kameyama and H.K. Kudo: Polym. J. et al. , 35, 213 (2003) T.A. Nishikubo, A .; Kameyama and H.K. Kudo: Am. Chem. Soc, 31, 363 K. Tsutsui, S .; Kishimoto, A. et al. Kameyama, T .; Nishikubo: Polym. Prep. Jpn. , 37, 1805 (1999) J. et al. R. Moran, S .; karbach and D.C. J. et al. Cram, J .; Am. Chem. Soc. 104, 5826 (1982) D. J. et al. Cram, K.M. D. Stewart, I.D. Goldberg and K.M. N. Trueblood, J, Am. Chem. Soc. 107, 2574 (1985). M.M. L. C. Quan and D.C. J. et al. Cram, J .; Am. Chem. Soc. , 113, 2754 (1991) J. et al. C. Sherman and D.C. J. et al. Cram, J .; Am. Chem. Soc. 111, 4527 (1989) J. et al. C. Sherman and D.C. J. et al. Cram, J .; Am. Chem. Soc. 111, 4527 (1989) P. Timerman, W.M. Verboom, F.M. C. J. et al. M.M. van Veggel, W.M. Hoorn and D.W. N. Reinhoudt, Angew. Chem. Int. Ed. Engl. 33, 1292 (1994)

  The present invention has been made in view of such problems of the prior art, and the object of the present invention is to facilitate chemical modification, to have a characteristic three-dimensional structure, and to include compounds It is an object of the present invention to provide a novel arene compound which is expected to be used as a compound and a production method thereof. In addition, the subject of the present invention is a novel arene-based compound derivative that has a characteristic three-dimensional structure and is expected to be used as an inclusion compound, etc., and is easily produced by chemical modification, and a method for producing the same. It is to provide.

  As a result of intensive studies to achieve the above-mentioned problems, the present inventors have found that the above-mentioned problems can be achieved by reacting an aromatic diol compound and an aromatic dialdehyde compound, and the present invention is completed. It came to.

  That is, according to the present invention, the following arene compounds, arene compound derivatives, methods for producing arene compounds, and methods for producing arene compound derivatives are provided.

  [1] A chemically modifiable phenolic compound obtained by reacting a raw material compound (A) represented by the following general formula (1) with a raw material compound (B) represented by the following general formula (2) An arene compound having a hydroxyl group in its molecular structure.

  In the general formula (1), X is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, or a substitution having 2 to 10 carbon atoms. Or an unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group having 7 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenoxy group, Independently represents 0 or 1.

  In the general formula (2), Y represents a monovalent substituent independently of each other, and n represents 0 or 1 independently of each other.

  [2] The arene compound according to [1], wherein the raw material compound (A) is 1,3-dihydroxybenzene.

  [3] The arene compound according to [1] or [2], wherein the raw material compound (B) is o-phthalaldehyde, m-phthalaldehyde, or p-phthalaldehyde.

  [4] An arene compound derivative in which a protecting group is introduced into the phenolic hydroxyl group of the arene compound according to any one of [1] to [3].

  [5] The arene compound derivative according to [4], wherein the protecting group is a tert-butoxycarbonyl group.

  [6] A method for producing an arene-based compound comprising a step of reacting a raw material compound (A) represented by the following general formula (1) and a raw material compound (B) represented by the following general formula (2).

  In the general formula (1), X is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, or a substitution having 2 to 10 carbon atoms. Or an unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group having 7 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenoxy group, Independently represents 0 or 1.

  In the general formula (2), Y represents a monovalent substituent independently of each other, and n represents 0 or 1 independently of each other.

  [7] The method for producing an arene compound according to [6], wherein the raw material compound (A) is 1,3-dihydroxybenzene.

  [8] The process for producing an arene compound according to [6] or [7], wherein the raw material compound (B) is o-phthalaldehyde, m-phthalaldehyde, or p-phthalaldehyde.

  [9] A method for producing an arene compound derivative, comprising a step of introducing a protective group into the phenolic hydroxyl group of the arene compound according to any one of [1] to [3].

  [10] The method for producing an arene compound derivative according to [9], wherein the protecting group is a tert-butoxycarbonyl group.

  The arene compounds of the present invention are easy to chemically modify, have a characteristic steric structure, and are expected to be used as inclusion compounds. Also, by chemically modifying the arene compounds of the present invention, application to curable compositions and resist compositions, use as inclusion compounds, use as high-function arene compound intermediates, etc. Expected to be used in a wide range of fields.

  The arene-based compound derivative of the present invention has a characteristic steric structure and is expected to be used as an inclusion compound. Moreover, it is easily manufactured by chemically modifying the above-mentioned arene compounds, and is applied to a curable composition or a resist composition, and used as an inclusion compound, and further, an arene system having a high function. It is expected to be used in a wide range of fields, such as as a compound intermediate.

  According to the method for producing an arene-based compound of the present invention, an arene-based compound that can be easily chemically modified, has a characteristic three-dimensional structure, and is expected to be used as an inclusion compound or the like is easily produced. be able to.

  According to the method for producing an arene compound derivative of the present invention, an arene compound derivative that has a characteristic steric structure and is expected to be used as an inclusion compound or the like can be easily produced by chemical employment.

  BEST MODE FOR CARRYING OUT THE INVENTION The best mode for carrying out the present invention will be described below, but the present invention is not limited to the following embodiment, and is based on the ordinary knowledge of those skilled in the art without departing from the gist of the present invention. It should be understood that modifications and improvements as appropriate to the following embodiments also fall within the scope of the present invention.

  The arene compound of the present invention is obtained by reacting the raw material compound (A) represented by the general formula (1) with the raw material compound (B) represented by the general formula (2). is there. The details will be described below.

(Raw compound (A))
The raw material compound (A) is an aromatic diol compound represented by the following general formula (1).

  In the general formula (1), X is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, or a substitution having 2 to 10 carbon atoms. Or an unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group having 7 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenoxy group, Independently represents 0 or 1.

  The raw material compound (A) represented by the general formula (1) is substituted or unsubstituted dihydroxybenzene. Specific examples of the raw material compound (A) include 1,3-dihydroxybenzene (resorcinol), 2-methylresorcinol, and 2-butylresorcinol. Among these, resorcinol and 2-methylresorcinol are preferable. In addition, these raw material compounds (A) can be used individually by 1 type or in combination of 2 or more types.

(Raw material compound (B))
The raw material compound (B) is an aromatic dialdehyde compound represented by the following general formula (2).

  In the general formula (2), Y represents a monovalent substituent independently of each other, and n represents 0 or 1 independently of each other.

  The raw material compound (B) represented by the general formula (2) is a substituted or unsubstituted phthalaldehyde. Specific examples of the raw material compound (B) include o-phthalaldehyde, m-phthalaldehyde, and p-phthalaldehyde. These raw material compounds (B) can be used individually by 1 type or in combination of 2 or more types.

(Reaction of raw material compound (A) and raw material compound (B))
The arene compound of the present invention comprises a raw material compound (A) and a raw material compound (B) in a solvent, for example, in the presence of a catalyst for 0.2 hours or more (preferably 48 hours or more), from room temperature (25 ° C.) to It can be produced by a dehydration condensation reaction under a temperature condition of 110 ° C. Examples of the solvent that can be used include alcohols such as ethanol, isopropanol, n-propanol, and n-butanol. In addition, it is preferable to select a solvent suitably according to the temperature of dehydration condensation reaction. Examples of the catalyst that can be used include acid catalysts such as hydrochloric acid.

  Although there is no restriction | limiting in particular in the molar ratio of a raw material compound (A) and a raw material compound (B), From a viewpoint of a yield, the value (molar ratio) of raw material compound (B) / raw material compound (A) is 0.1 It is preferably in the range of 0.6, more preferably in the range of 0.2 to 0.5, still more preferably in the range of 0.2 to 0.3, and 0.2 to 0.25. It is particularly preferable that the range is

  The substrate concentration in the reaction solution (the total concentration of the raw material compound (A) and the raw material compound (B)) is not particularly limited, but is preferably 2 mol / l or more from the viewpoint of yield, and 4 mol / l. 1 or more is more preferable, and the range of 4 to 10 mol / l is particularly preferable.

(3D structure)
The steric structure of the arene compound of the present invention obtained by the above reaction is not particularly limited. The three-dimensional structure of the arene compound of the present invention is presumed to be, for example, a ladder-type cyclic oligomer as shown in FIG. 1A, a ladder-type polymer as shown in FIG. 1B, a branched polymer as shown in FIG. Is done. Moreover, it is estimated that the three-dimensional structure of the arene compound of the present invention is, for example, a structure obtained by combining these three-dimensional structures shown in FIGS. 1A, 1B, and 1C. Or the case where it obtains as a mixture of the compound which has each three-dimensional structure represented by FIG. 1A, FIG. 1B, and FIG. 1C by making a raw material compound (A) and a raw material compound (B) react is assumed.

  The arene-based compound of the present invention has a phenolic hydroxyl group (—OH group) that can be chemically modified in its molecular structure. Therefore, various substituents can be introduced into this phenolic hydroxyl group. Specific examples of the substituent that can be introduced include a protective group such as a tert-butoxycarbonyl (Boc) group, a group having a polymerizable functional group, a group having an alkali-soluble group, a substituted or unsubstituted alkyl group, and the like. Can be mentioned.

  Specific examples of the polysynthetic functional group include a group having a polymerizable unsaturated structure and a group having a cyclic ether structure. More specifically, a vinyl group, a vinylidene group, an acryloyl group, a methacryloyl group, a substituted or unsubstituted glycidyl group, a substituted or unsubstituted oxetanyl group, a substituted or unsubstituted spiro orthoester group, and the like can be given. Further, examples of the alkali-soluble group include a carboxyl group, an amino group, a sulfonamide group, a sulfonic acid group, and a phosphoric acid group.

  EXAMPLES Hereinafter, although this invention is demonstrated concretely based on an Example, this invention is not limited to these Examples. In the examples and comparative examples, “parts” and “%” are based on mass unless otherwise specified.

  [Measurement of Infrared Absorption Spectrum (IR)]: The infrared absorption spectrum (IR) was measured using a trade name “Nicolet 380” manufactured by Thermo Electron.

[Measurement of nuclear magnetic resonance spectrum ( ¹ H-NMR)]: A nuclear magnetic resonance spectrum ( ¹ H-NMR) was measured using a trade name “JNM-2500” manufactured by JEOL.

  [Measurement of Number Average Molecular Weight (Mn)]: The number average molecular weight (Mn) of the synthesized sample was measured using a column (trade name “HLC-8220”) manufactured by Tosoh Corporation, flow rate: 0 to 600 ml / min, elution. Measurement was performed by size exclusion chromatography (SEC) using polystyrene as a standard under the analysis conditions of solvent: DMF, column temperature: 40 ° C.

[Measurement of the thermal decomposition temperature _{(T d)]:} using Seiko Instruments Inc. under the trade name "SSC / 5200 DSC120", under a nitrogen atmosphere, the thermal decomposition temperature at a heating rate of 10 ℃ / min _{(T d)} It was measured.

Example 1
In a 50 ml eggplant flask containing a rotor, 2.2 g (20 mmol (functional group equivalent: 40 mmol)) of resorcinol and 3 ml of ethanol were added, and resorcinol was dissolved in ethanol. After adding 3 ml of concentrated hydrochloric acid as a catalyst, 0.67 g (5 mmol (functional group equivalent: 10 mmol)) of m-phthalaldehyde (m-PA) dissolved in 6 ml of hot ethanol was slowly added dropwise under ice cooling. The reaction was stirred for 48 hours at 0 ° C. After completion of the reaction, the produced solid was washed with ether to obtain 1.56 g of a yellow solid. Charts showing IR and ¹ H-NMR measurement results of the obtained yellow solid are shown in FIGS. 2 and 3, respectively.
IR (film method, cm ⁻¹ ): 3374 (ν _OH ); 1607, 1507, 1430 (ν _{C═C (aromatic)} )

(Example 2)
In a 50 ml eggplant flask containing a rotor, 2.2 g (20 mmol (functional group equivalent: 40 mmol)) of resorcinol and 1.5 ml of ethanol were added, and resorcinol was dissolved in ethanol. After adding 1.5 ml of concentrated hydrochloric acid as a catalyst, 0.67 g (5 mmol (functional group equivalent: 10 mmol)) of m-phthalaldehyde (m-PA) dissolved in 3 ml of hot ethanol was slowly added dropwise under ice cooling. The reaction was allowed to stir at 80 ° C. for 48 hours. After completion of the reaction, the produced solid was washed with ether to obtain 1.54 g of a yellow solid (Table 1).

(Example 3)
Except for using 3 ml of ethanol, 3 ml of concentrated hydrochloric acid, and 6 ml of hot ethanol, 1.56 g of a yellow solid was obtained in the same manner as in Example 2 described above (Table 1).

Example 4
In a 50 ml eggplant flask containing a rotor, 2.2 g (20 mmol) of resorcinol and 3 ml of ethanol were added, and resorcinol was dissolved in ethanol. After adding 3 ml of concentrated hydrochloric acid as a catalyst, 0.27 g (2 mmol) of m-phthalaldehyde (m-PA) dissolved in 6 ml of hot ethanol was slowly added dropwise under ice cooling, followed by stirring at 80 ° C. for 48 hours. Reacted. After completion of the reaction, the produced solid was washed with ether to obtain 0.39 g of a yellow solid. The number average molecular weight (Mn) of the obtained yellow solid was 1880. In addition, the chromatogram (elution chart) which shows the analysis result by size exclusion chromatography (SEC) is shown in FIG.

(Examples 5 to 11)
m-phthalaldehyde (m-PA) was added to 0.4 g (3 mmol), 0.53 g (4 mmol), 0.67 g (5 mmol), 0.8 g (6 mmol), 0.93 g (7 mmol), 1.06 g ( 8 mmol) and 1.34 g (10 mmol) were used, and a yellow solid was obtained in the same manner as in Example 4 described above. The measurement results of yield (g) and number average molecular weight (Mn) are shown in Table 2. Further, FIG. 4 shows a chromatogram (elution chart) showing an analysis result by size exclusion chromatography (SEC).

Example 12
In a 50 ml eggplant flask containing a rotor, 2.2 g (20 mmol (functional group equivalent: 40 mmol)) of resorcinol and 3 ml of ethanol were added, and resorcinol was dissolved in ethanol. After adding 3 ml of concentrated hydrochloric acid as a catalyst, 0.67 g (5 mmol (functional group equivalent: 10 mmol)) of o-phthalaldehyde (o-PA) dissolved in 6 ml of hot ethanol was slowly added dropwise under ice cooling. The reaction was allowed to stir at 0 ° C. for 0.5 hour. After completion of the reaction, the produced solid was washed with ether to obtain 1.38 g of a brown solid (Table 3). FIG. 5 shows a chromatogram (elution chart) showing the analysis result of the obtained brown solid by size exclusion chromatography (SEC). In addition, charts showing IR and ¹ H-NMR measurement results of the obtained brown solid are shown in FIGS. 6 and 7, respectively.
IR (film method, cm ⁻¹ ): 3376 (ν _OH ); 1602, 1504, 1433 (ν _{C═C (aromatic)} )

(Example 13)
In a 50 ml eggplant flask containing a rotor, 2.2 g (20 mmol (functional group equivalent: 40 mmol)) of resorcinol and 3 ml of ethanol were added, and resorcinol was dissolved in ethanol. After adding 3 ml of concentrated hydrochloric acid as a catalyst, 0.67 g (5 mmol (functional group equivalent: 10 mmol)) of p-phthalaldehyde (p-PA) dissolved in 6 ml of hot ethanol was slowly added dropwise under ice cooling. The reaction was stirred for 3 hours at ° C. After completion of the reaction, the produced solid was washed with ether to obtain 0.67 g of a brown solid (Table 3). The chromatogram (elution chart) which shows the analysis result by size exclusion chromatography (SEC) of the obtained brown solid is shown in FIG. Further, charts showing IR and ¹ H-NMR measurement results of the obtained brown solid are shown in FIGS. 9 and 10, respectively.
IR (film method, cm ⁻¹ ): 3386 (ν _OH ); 1614, 1506, 1431 (ν _{C═C (aromatic)} )

(Example 14)
In a 50 ml flask containing a rotor, 3.2 g (2.5 mmol) of the yellow solid obtained in Example 1 (hereinafter referred to as “m-cyclic”), 0.65 g of tetrabutylammonium bromide (TBAB) (2. 0 mmol) and 30 ml of pyridine were added, and m-cyclic was dissolved in pyridine. Thereafter, 13.1 g (60 mmol) of di-tert-butyl-di-carbonate (DiBoc) was added dropwise under ice cooling, and the mixture was reacted at room temperature for 48 hours. After completion of the reaction, the reaction solution was diluted with chloroform, washed 3 times with 1N hydrochloric acid and once with tap water, and the organic layer was dried using anhydrous magnesium sulfate. The anhydrous magnesium sulfate was filtered off, concentrated, and then separated by silica gel chromatography (developing solvent (volume ratio) = ethyl acetate: n-hexane = 1: 1), and the developing solvent was distilled off under reduced pressure to give 6.0 g of yellow A solid (hereinafter referred to as “m-cyclic-Boc”) was obtained (yield 83%). The thermal decomposition temperatures of the obtained m-cyclic-Boc were T _d ^5% = 163 ° C and T _d ^10% = 166 ° C. Table 4 shows the measurement results of the thermal decomposition temperatures of m-cyclic and m-cyclic-Boc. In addition, charts showing IR and ¹ H-NMR measurement results of the obtained m-cyclic-Boc are shown in FIGS. 11 and 12, respectively. Furthermore, the graph which shows the thermal decomposition curve of m-cyclic and m-cyclic-Boc is shown in FIG.
IR (film method, cm ⁻¹ ): 2981, 2934 (ν _C—H ); 1759 (ν _{C═O (carbonate)} ); 1605, 1496, 1458 (ν _{C = C (aromatic)} ); 1370 (ν _{C -H (t-butyl)} )

From the IR measurement results, it is clear that the absorption derived from the aromatic hydroxyl group present in the vicinity of 3500 cm ⁻¹ disappeared due to the chemical modification. Moreover, it is clear from the measurement result of ¹ H-NMR that the signal derived from the proton of the hydroxyl group disappeared. Furthermore, since the integrated values of ¹ H-NMR are also in good agreement, it is considered that the Boc group could be introduced at a ratio of 100% with respect to the phenolic hydroxyl group of m-cyclic as a raw material.

  Further, from the results shown in Table 4 and FIG. 13, it is clear that m-cyclic-Boc is thermally decomposed in two stages and, after the first stage of thermal decomposition, shows a thermal decomposition curve similar to that of m-cyclic. is there. Therefore, it is estimated that the Boc group is introduced with respect to the phenolic hydroxyl group of m-cyclic.

  The arene compounds of the present invention have a characteristic steric structure and are easily chemically modified. For this reason, the arene compounds of the present invention are expected to be used as compounds exhibiting special functions including inclusion compounds.

It is a schematic diagram which shows an example (ladder type | mold cyclic oligomer) of the three-dimensional structure of the arene type compound of this invention. It is a schematic diagram which shows the other example (ladder type polymer) of the three-dimensional structure of the arene compound of this invention. It is a schematic diagram which shows the further another example (branched polymer) of the three-dimensional structure of the arene-type compound of this invention. 2 is a chart showing measurement results of infrared absorption spectrum (IR) of a yellow solid obtained in Example 1. FIG. 2 is a chart showing measurement results of nuclear magnetic resonance spectrum ( ¹ H-NMR) of a yellow solid obtained in Example 1. FIG. It is a chromatogram (elution chart) which shows the analysis result by size exclusion chromatography (SEC) of the yellow solid obtained in Examples 4-10. It is a chromatogram (elution chart) which shows the analysis result by size exclusion chromatography (SEC) of the brown solid obtained in Example 12. 10 is a chart showing measurement results of infrared absorption spectrum (IR) of a brown solid obtained in Example 12. 10 is a chart showing measurement results of nuclear magnetic resonance spectrum ( ¹ H-NMR) of a brown solid obtained in Example 12. It is a chromatogram (elution chart) which shows the analysis result by size exclusion chromatography (SEC) of the brown solid obtained in Example 13. 10 is a chart showing measurement results of infrared absorption spectrum (IR) of a brown solid obtained in Example 13. Is a chart showing the results of measurement of the nuclear magnetic resonance spectrum of a brown solid obtained in Example 13 ^{(1 H-NMR).} It is a chart which shows the measurement result of the infrared absorption spectrum (IR) of the yellow solid (m-cyclic-Boc) obtained in Example 14. Is a chart showing the measurement results of the yellow solid obtained in Example 14 (m-cyclic-Boc) Nuclear magnetic resonance spectra ⁽¹ H-NMR). It is a graph which shows the thermal decomposition curve of m-cyclic and m-cyclic-Boc.

Claims (10)

A chemically modifiable phenolic hydroxyl group obtained by reacting a raw material compound (A) represented by the following general formula (1) with a raw material compound (B) represented by the following general formula (2) An arene compound contained in the molecular structure.

(In the general formula (1), X is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, or a group having 2 to 10 carbon atoms. A substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group having 7 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenoxy group, m is Shows 0 or 1 independently of each other)

(In the general formula (2), Y represents a monovalent substituent independently of each other, and n represents independently of each other 0 or 1)   The arene compound according to claim 1, wherein the raw material compound (A) is 1,3-dihydroxybenzene.   The arene compound according to claim 1 or 2, wherein the raw material compound (B) is o-phthalaldehyde, m-phthalaldehyde, or p-phthalaldehyde.   The arene type compound derivative in which the protecting group was introduce | transduced into the said phenolic hydroxyl group of the arene type compound as described in any one of Claims 1-3.   The arene compound derivative according to claim 4, wherein the protecting group is a tert-butoxycarbonyl group. A method for producing an arene compound, which comprises a step of reacting a raw material compound (A) represented by the following general formula (1) and a raw material compound (B) represented by the following general formula (2).

(In the general formula (1), X is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, or a group having 2 to 10 carbon atoms. A substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group having 7 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenoxy group, m is Shows 0 or 1 independently of each other)

(In the general formula (2), Y represents a monovalent substituent independently of each other, and n represents independently of each other 0 or 1)   The method for producing an arene compound according to claim 6, wherein the raw material compound (A) is 1,3-dihydroxybenzene.   The method for producing an arene-based compound according to claim 6 or 7, wherein the raw material compound (B) is o-phthalaldehyde, m-phthalaldehyde, or p-phthalaldehyde.   The manufacturing method of an arene type compound derivative which has the process of introduce | transducing a protecting group into the said phenolic hydroxyl group of the arene type compound as described in any one of Claims 1-3.   The method for producing an arene-based compound derivative according to claim 9, wherein the protecting group is a tert-butoxycarbonyl group.

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