JPH01216941A - Production of diarylmethane compound - Google Patents
Production of diarylmethane compoundInfo
- Publication number
- JPH01216941A JPH01216941A JP4128188A JP4128188A JPH01216941A JP H01216941 A JPH01216941 A JP H01216941A JP 4128188 A JP4128188 A JP 4128188A JP 4128188 A JP4128188 A JP 4128188A JP H01216941 A JPH01216941 A JP H01216941A
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- group
- compound
- formula
- para
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims abstract description 21
- -1 aniline compound Chemical class 0.000 claims abstract description 11
- 235000019445 benzyl alcohol Nutrition 0.000 claims abstract description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003377 acid catalyst Substances 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 abstract description 9
- 125000003118 aryl group Chemical group 0.000 abstract description 8
- NVNXWNOHZFUTRO-UHFFFAOYSA-N 3h-2-benzofuran-1-one;9h-fluorene Chemical compound C1=CC=C2C(=O)OCC2=C1.C1=CC=C2CC3=CC=CC=C3C2=C1 NVNXWNOHZFUTRO-UHFFFAOYSA-N 0.000 abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003021 water soluble solvent Substances 0.000 abstract description 3
- 125000002252 acyl group Chemical group 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 125000000304 alkynyl group Chemical group 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241001080061 Talides Species 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Chemical class 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011707 mineral Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical class ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical class ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】 （発明の分野） 本発明はジアリールメタン化合物の製造法に関する。[Detailed description of the invention] (Field of invention) The present invention relates to a method for producing diarylmethane compounds.
（従来の技術）
近年、レーザー光の発展とともに、近赤外部に吸収を有
する記録材料を用いたシステムの開発が盛んに行なわれ
ている。(Prior Art) In recent years, with the development of laser light, systems using recording materials that absorb near-infrared light have been actively developed.
電子供与性の無色染料と電子受容性化合物を便用した記
録システムに於ては、その発色部が近赤外部に吸収を有
する無色染料がいくつか開発されている。In a recording system that conveniently uses an electron-donating colorless dye and an electron-accepting compound, several colorless dyes have been developed whose coloring portion absorbs in the near-infrared region.
例えば、フルオレンフタリド系化合物（特開昭ｊター／
Ｆ５Ｆ７７７など）、フルオランフタリド系化合物（特
開昭ｔ／−２１１１−１ｉｔ！など）チオフルオラン７
タリド系化合物（特開昭ｊターｌ≠１６り！など）、ジ
ビニル化合物（特公昭ｒをｊり弘Ｏなど）等が開示され
ている。For example, fluorene phthalide compounds (JP-A-Shojter/
F5F777, etc.), fluorane phthalide compounds (JP-A-Sho t/-2111-1it!, etc.), thiofluorane 7
Talide-based compounds (Japanese Patent Publication No. 2003-110000, etc.), divinyl compounds (Japanese Patent Publication No. 2003-120001, etc.), and the like have been disclosed.
これらの中でもフルオレンフタリド系化合物は開示数が
多く、有用な物質であると考えられる。Among these, fluorene phthalide compounds have been disclosed in many cases and are considered to be useful substances.
本発明によって製造されるジアリールメタン化合物はフ
ルオレン７タリド系無色染料の中間体として使用できる
にもかかわらず現在まで全く検討されていなかつ九。Although the diarylmethane compound produced by the present invention can be used as an intermediate for fluorene-7thallide-based colorless dyes, it has not been studied at all to date.
そこで我々は鋭意研究を重ね、パラ置換ベンジルアルコ
ールと置換アニリン化会物を縮合させジアリールメタン
化合物を得る方法を開発し、本発明を完成するに至った
。Therefore, we conducted extensive research and developed a method to obtain a diarylmethane compound by condensing a para-substituted benzyl alcohol and a substituted aniline compound, thereby completing the present invention.
（発明の目的）
従って本発明の目的はジアリールメタン化合物の製造法
を提供することである。OBJECTS OF THE INVENTION It is therefore an object of the present invention to provide a method for producing diarylmethane compounds.
（発明の構成）
本発明の目的はパラ置換ベンジルアルコールと置換ア＝
ＩＪン化化合物金融触媒存在下、縮合させることを特
徴とするジアリールメタン化合物の製造法によって達成
され友。(Structure of the Invention) The object of the present invention is to combine para-substituted benzyl alcohol and substituted a=
This has been achieved by a method for producing a diarylmethane compound, which is characterized by condensing an IJ compound in the presence of a financial catalyst.
本発明でいう置換基とはアルキル基、アリール基、アラ
ルキル基、アルコキシ基、アリールオキシ基、アミン基
、置換アミノ基、ニトロ基、シアノ基、置換カルバモイ
ル基、置換スルファモイル基、ａｍオキシカルボニ、ル
基、置換オキシスルホニル基、ハロゲン原子、及び水素
原子を意味し、無置換でも一＋１換でも多置換でもかま
わない。The substituents referred to in the present invention are alkyl groups, aryl groups, aralkyl groups, alkoxy groups, aryloxy groups, amine groups, substituted amino groups, nitro groups, cyano groups, substituted carbamoyl groups, substituted sulfamoyl groups, amoxycarbonyl groups, , means a substituted oxysulfonyl group, a halogen atom, and a hydrogen atom, and may be unsubstituted, monosubstituted, or polysubstituted.
好ましくは
本発明で用いるノラ＃換ベンジルアルコールは下記−数
式（１）で表わされる。Preferably, the benzyl alcohol used in the present invention is represented by the following formula (1).
（上式中Ｒ１は置換アミノ基及びアルコキシ基ｋＲ２は
置換アミノ基、アルコキシ基、アルキル基、ハロゲン原
子、及び水素原子を表わす。）置換アニｌＪン化合物に
ついては下記−数式（ＩＩ）で表わされる。(In the above formula, R1 represents a substituted amino group and an alkoxy group kR2 represents a substituted amino group, an alkoxy group, an alkyl group, a halogen atom, and a hydrogen atom.) The substituted anil compound is represented by the following formula (II). .
（上式中Ｒ３は水素原子、［ｆｔ置換アミノ基びアルコ
キシ基をＲ４は置換アミノ基、アルコキシ基、アルキル
基、ハロゲン原子、および水素原子’ＴｈＲ５は水素原
子、アシル基、ベンゾイル基及び置換スルホニル基金表
わす。）
上記（１）および（ＩＩ）の縮合反応による生成物は下
記−数式（１）で表わされる。(In the above formula, R3 is a hydrogen atom; The product of the condensation reaction of (1) and (II) above is represented by the following formula (1).
（上式中Ｒ１、Ｒ２、Ｒ３、Ｒ４及びＲ５は式（１）及
び（ＩＩ）で示した置換基と同じ意味を表わす。）
上式（り〜（ＩＩ）においてＲ１、Ｒ２、Ｒ３及びＲ４
が置換アミノ基を表わす場合、置換アミノ基は一般式１
）で表わされる。(In the above formula, R1, R2, R3, R4 and R5 represent the same meanings as the substituents shown in formulas (1) and (II).)
represents a substituted amino group, the substituted amino group has the general formula 1
).
Ｒ６及びＲ７は同一でも異なっていてもよく、アルキル
基、シクロアルキル基、アルケニル基、アルキニル基、
およびアリール基を表わす。またＲ６とＲ７は互いに結
合して環を形成していてもよい。）
上式中Ｒ６及びＲ７で表わされる置換基は更に、アルキ
ル基、アルコキシ基、アルキルチオ基、アリール基、ア
リールオキシ基、ハロゲン原子、ニトロ基、７７ノ基、
置換アミン基、置換カルバモイル基、置換スルファモイ
ル基、置換オキシカルボニル基、ま九は置換オキシスル
ホニル基へテロ環等で置換されていてもよい。これらの
置換基はさらに置換基を有していてもよい。R6 and R7 may be the same or different, and are an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group,
and represents an aryl group. Further, R6 and R7 may be bonded to each other to form a ring. ) The substituents represented by R6 and R7 in the above formula further include an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, a halogen atom, a nitro group, a 77 group,
A substituted amine group, a substituted carbamoyl group, a substituted sulfamoyl group, a substituted oxycarbonyl group, and a substituted oxysulfonyl group may be substituted with a heterocycle or the like. These substituents may further have a substituent.
具体的にはＲ６およびＲ７として−ＣＨ３、−Ｃ，Ｈ２
ｎ ＩＸＹ、−ＣｎＨ２ｎ ３ＸＹ、−ＣｎＨ２ｎ
−ａ、−ＣｎＨ２ｎｏＣｍＨ２ｍ−ＩＸＹ。Specifically, as R6 and R7 -CH3, -C,H2
n IXY, -CnH2n 3XY, -CnH2n
-a, -CnH2noCmH2m-IXY.
（ｎは２からｉｏの整数、ｍは１から３の整数、Ｘおよ
びＹは水素原子、ハロゲン原子、アルキル基、アリール
基、アルコキシ基、アリールオキシ基、アシル基、ニト
ロ基、シアノ基および置換アミン基などが好ましい例で
ありχ
Ｒ１とＲ２またはＲ３とＲ４が環を形成する場（ｉは≠
から７の整数を表わす）などが好ましい例である。(n is an integer from 2 to io, m is an integer from 1 to 3, X and Y are hydrogen atoms, halogen atoms, alkyl groups, aryl groups, alkoxy groups, aryloxy groups, acyl groups, nitro groups, cyano groups, and substituted A preferred example is an amine group, and χ where R1 and R2 or R3 and R4 form a ring (i is ≠
(representing an integer from 7 to 7) is a preferable example.
Ｒ１，Ｒ２、Ｒ３及びＲ４がアルコキシ基を表わす場合
、アルコキシ基は一般式（Ｖ）で表わされる
−０−Ｒ８（Ｖ）
（上式中Ｒ８は一般式（ｆ’ｖ’）におけるＲ６と同じ
意味の基を表わす）
Ｒ２及びＲ４がアルキル基を表わす場合炭素数ｌから２
０が好ましく待には１から／、２が好ましい。この場合
、アルキル基は更にアルキル基、アルコキシ基、アルキ
ルチオ基、アリール基、アリールオキシ基、ハロゲン原
子等で置換されていてもよい。これらの置換基は更に置
換基を有していてもよい。When R1, R2, R3 and R4 represent an alkoxy group, the alkoxy group is represented by the general formula (V) -0-R8(V) (in the above formula, R8 is the same as R6 in the general formula (f'v') When R2 and R4 represent an alkyl group, the number of carbon atoms is 1 to 2.
0 is preferable, and 1 to 2 is preferable. In this case, the alkyl group may be further substituted with an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, a halogen atom, or the like. These substituents may further have a substituent.
一般式（１）〜（［１）においてＲ５で示される基は置
換基を有していてもよく、置換基としては７Ａ／キル基
、アリール基、シアノ基、ニトロ基、トリフルオロメチ
ル基、ノ１０ゲン原子が好ましく、更に置換基金有して
いてもよい。具体的にはＲ５（Ｚはアルキル基、アリー
ル基、シアノ基、ニトロ基、トリフルオロメチル基、及
び）・ロゲン原子を表わしｊは１から１０の整数を示す
）
次に本発明に係るジアリールメタン化合物の具体例を示
すが、本発明はこれらに限定されるものではない。The group represented by R5 in general formulas (1) to ([1)] may have a substituent, and examples of the substituent include a 7A/kyl group, an aryl group, a cyano group, a nitro group, a trifluoromethyl group, A 10-gen atom is preferred, and may further have a substituent group. Specifically, R5 (Z represents an alkyl group, an aryl group, a cyano group, a nitro group, a trifluoromethyl group, and a ).logen atom, and j represents an integer from 1 to 10) Next, the diarylmethane according to the present invention Although specific examples of the compounds are shown, the present invention is not limited thereto.
本発明に係る製造方法は水溶性溶媒中、或いは無溶媒で
酸触媒の存在下室温或いは加熱してパラ置換ベンジルア
ルコールと置換アニリン化合物を脱水縮合させるもので
ある。The production method according to the present invention involves dehydrating and condensing para-substituted benzyl alcohol and a substituted aniline compound in a water-soluble solvent or without a solvent in the presence of an acid catalyst at room temperature or with heating.
酸触媒としては濃硫酸、濃塩酸、臭化水素水、パラトル
エンスルホン酸、メタンスルホン酸、オキシ塩化リン、
三塩化リン、五塩化リン、リン酸、ポリリン酸及び鉱酸
が好ましい。Acid catalysts include concentrated sulfuric acid, concentrated hydrochloric acid, hydrogen bromide, para-toluenesulfonic acid, methanesulfonic acid, phosphorus oxychloride,
Preferred are phosphorus trichloride, phosphorus pentachloride, phosphoric acid, polyphosphoric acid and mineral acids.
水溶性溶媒としては低級アルコール類、アセトン、Ｎ、
Ｎ−ジメチルホルムアミド、Ｎ、Ｎ−ジメチルアセトア
ミド、ジメチルスルホキシド、及びアセトニトリルが好
ましく、待にはメタノール、エタノール、及びイソプロ
パツールなどの低級アルコール類が好ましい。Water-soluble solvents include lower alcohols, acetone, N,
N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and acetonitrile are preferred, and lower alcohols such as methanol, ethanol, and isopropanol are preferred.
これらは水と適当な割合で混合して用いてもよい。These may be used by mixing with water in an appropriate ratio.
加熱する場合は反応温度としては！θ〜１ｊ００Ｃが好
ましく詩には６！〜／コＯ０Ｃが好−ましい。When heating, the reaction temperature is! θ~1j00C is preferable and 6 for poetry! ~/ko00C is preferred.
このようにして製造された一般式（ＩＩＩ）で示される
ジアリールメタン化合物は、無置換のアミノ基が分子内
に存在する場合はアセチル基等の適当な保護基を導入し
友のち、酸化し、脱保護基或いは加水分解することによ
ってコーアミノベンゾフェノン化合物に導かれる。これ
は、例えば、２位のアミノ基ｔジアゾニウム塩に変え次
のち、分子内閉環させることによってターフルオレノン
化合物に導かれる。ターフルオレノン化合物は、フルオ
レンフタリド系無色染料の重要な中間体である。The diarylmethane compound represented by the general formula (III) thus produced is oxidized after introducing an appropriate protecting group such as an acetyl group when an unsubstituted amino group is present in the molecule. A co-aminobenzophenone compound is obtained by deprotection or hydrolysis. This is, for example, converted into a diazonium salt with an amino group at the 2-position, and then subjected to intramolecular ring closure to lead to a terfluorenone compound. Terfluorenone compounds are important intermediates for fluorene phthalide colorless dyes.
（実施例）
以下、実施例により本発明上説明するが本発明はこれら
の実施例に限定されるものではない。(Examples) The present invention will be described below with reference to Examples, but the present invention is not limited to these Examples.
実ｍ例／。Actual example/.
パラーＮ、Ｎ−ジエチルアミノベンジルアルコールタＱ
、≠を及びメターＮ、Ｎ−ジエチルアミノアセトアニリ
ドｌ０Ｊｆをメタノール２００ｍ１、水≠００ｒｎｌ及
び製塩＠１００ｒｒｔｌの混合溶媒に加えたのち加熱、
還流を１時間行なった。反応混合物を氷水１ｔにあけた
のち、希苛性ソーダ水でゆっくりと中和し比。析出し几
沈殿をＰ取し、メタノ−ルー酢酸エチルで再結晶、化合
物（５）’ｉ／ｊｊｆ得友。収率１３％ 。Para-N,N-diethylaminobenzylalcoholtaQ
, ≠ and 10 Jf of meta-N,N-diethylaminoacetanilide were added to a mixed solvent of 200 ml of methanol, ≠00 rnl of water and 100 rrtl of salt, and then heated.
Reflux was carried out for 1 hour. The reaction mixture was poured into 1 ton of ice water, and then slowly neutralized with dilute caustic soda water. The precipitate was collected and recrystallized from methanol-ethyl acetate to obtain compound (5)'i/jjf. Yield 13%.
ｍ、ｐ、／コ４！−／２！０Ｃ
Ｍ／６＝Ｊｔ７
１Ｈ−ＮＭＲ（ＣＤＣＩ ｓ、δ１）、／ 、１０（１
２Ｈ１ｔ）、１．に７（３Ｈ％り、３．２３（ｒＨ，ｑ
ｒ）、Ｊ、ｔ７（２Ｈ，Ｓ）、ａ。m, p, /ko4! -/2!0C M/6=Jt7 1H-NMR (CDCI s, δ1), / , 10 (1
2H1t), 1. 7(3H%ri, 3.23(rH,q)
r), J, t7(2H,S), a.
参〇（／Ｈ，ｄｄ）、ｊ、ｆｊ（，２Ｈ％ｄ）、６゜７
０−７．０２（ｊＨ，ｍ）、７．３０（／Ｈ１ｍ）
特許出願人 富士写真フィルム株式会社手続補正書（自
制
昭和６３年ゲ月に日〇(/H,dd),j,fj(,2H%d),6゜7
0-7.02 (jH, m), 7.30 (/H1m) Patent applicant Fuji Photo Film Co., Ltd. Procedural amendment
Claims (1)
触媒の存在下、縮合させることを特徴とする、ジアリー
ルメタン化合物の製造法。A method for producing a diarylmethane compound, which comprises condensing para-substituted benzyl alcohol and a substituted aniline compound in the presence of an acid catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4128188A JPH01216941A (en) | 1988-02-24 | 1988-02-24 | Production of diarylmethane compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4128188A JPH01216941A (en) | 1988-02-24 | 1988-02-24 | Production of diarylmethane compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01216941A true JPH01216941A (en) | 1989-08-30 |
Family
ID=12604064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4128188A Pending JPH01216941A (en) | 1988-02-24 | 1988-02-24 | Production of diarylmethane compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01216941A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999048859A1 (en) * | 1998-03-20 | 1999-09-30 | Bristol-Myers Squibb Company | Aryloxyanilides and related compounds |
| JP2005060387A (en) * | 2003-07-29 | 2005-03-10 | Mitsubishi Chemicals Corp | Manufacturing method of arylamine derivative and methanol derivative used for manufacturing the same |
-
1988
- 1988-02-24 JP JP4128188A patent/JPH01216941A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999048859A1 (en) * | 1998-03-20 | 1999-09-30 | Bristol-Myers Squibb Company | Aryloxyanilides and related compounds |
| US6090854A (en) * | 1998-03-20 | 2000-07-18 | Bristol-Meyers Company | Aryloxyanilides and related compounds |
| JP2005060387A (en) * | 2003-07-29 | 2005-03-10 | Mitsubishi Chemicals Corp | Manufacturing method of arylamine derivative and methanol derivative used for manufacturing the same |
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