JP2007204390A5 - - Google Patents

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JP2007204390A5
JP2007204390A5 JP2006022421A JP2006022421A JP2007204390A5 JP 2007204390 A5 JP2007204390 A5 JP 2007204390A5 JP 2006022421 A JP2006022421 A JP 2006022421A JP 2006022421 A JP2006022421 A JP 2006022421A JP 2007204390 A5 JP2007204390 A5 JP 2007204390A5
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Claims (4)

一般式(１)
Figure 2007204390
 (式中、R1は、水素原子、炭素数1〜15のアルキル基、少なくとも一つのハロゲンにより置換された炭素数1〜15のアルキル基、炭素数2〜15のアルケニル基又は少なくとも一つのハロゲンにより置換された炭素数2〜15のアルケニル基を表し、これらの基中に存在する1個又は2個以上のCH2基はそれぞれ独立してO原子が相互に直接結合しないものとして -O-、-S-、-CO-、-COO-、-OCO-又は-OCO-O-により置き換えられても良く、
A1は、
(a) トランス-1,4-シクロへキシレン基(この基中に存在する1個のCH2基又は隣接していない2個以上のCH2基は -O- 及び又は -S- に置き換えられてもよい)
(b) 1,4-フェニレン基(この基中に存在する1個のCH2基又は隣接していない2個以上のCH2基は -N- に置き換えられてもよい)
(c) 1,4-シクロヘキセニレン、1,4-ビシクロ(2.2.2)オクチレン、ピペリジン-1,4-ジイル、ナフタレン-2,6-ジイル、デカヒドロナフタレン-2,6-ジイル及び1,2,3,4-テトラヒドロナフタレン-2,6-ジイル
からなる群より選ばれる基であり、上記の基(a)、基(b)、基(c)はCN又はハロゲンで置換されていても良く、aは0又は1であり、さらにR1-A1-は以下の構造、
Figure 2007204390
 （式中、nは1又は2を表す。）であっても良く、
Z1は-COO-、-OCO-、-CH2O-、-OCH2-、-CH2CH2-、-CH=CH-、-C≡C-、-(CH2)4-、-CH=CH-CH2CH2-、-CH2CH2-CH=CH- 又は単結合を表し、
Xは塩素原子、臭素原子、ヨウ素原子、トリフルオロメタンスルホネート、メタンスルホネート、p-トルエンスルホネート、ホウ酸、三フッ化ホウ素、ジアルキルホウ素、トリアルキルシラン、モノ及びジアルコキシシラン、モノ及びジフルオロシランを表し、L1、L2、L3及びL4はそれぞれ独立してフッ素原子又は水素原子を表すが、L1、L2、L3又はL4の少なくとも一つはフッ素原子を表す)で表される化合物に、一般式(２)
Figure 2007204390
 (式中、R2は、水素原子、炭素数1〜15のアルキル基、少なくとも一つのハロゲンにより置換された炭素数1〜15のアルキル基、炭素数2〜15のアルケニル基又は少なくとも一つのハロゲンにより置換された炭素数2〜15のアルケニル基を表し、これらの基中に存在する1個又は2個以上のCH2基はそれぞれ独立してO原子が相互に直接結合しないものとして -O-、-S-、-CO-、-COO-、-OCO-又は-OCO-O-により置き換えられても良い)
で表されるアルコールを反応させることを特徴とする一般式(３)
Figure 2007204390
 (式中、R1、A1、Z1、L1、L2、L3、又はL4は一般式（１）のものと同じものを示し、R2は一般式(２)と同じ意味を表す)で表されるハイドロキノン誘導体の製造方法。 General formula (1)
Figure 2007204390
 Wherein R 1 is a hydrogen atom, an alkyl group having 1 to 15 carbon atoms, an alkyl group having 1 to 15 carbon atoms substituted by at least one halogen, an alkenyl group having 2 to 15 carbon atoms or at least one halogen. -O- represents an alkenyl group having 2 to 15 carbon atoms that is substituted by, and one or two or more CH 2 groups present in these groups are independently defined as those in which O atoms are not directly bonded to each other. , -S-, -CO-, -COO-, -OCO- or -OCO-O-
A 1 is
(a) trans-1,4-cyclohexylene group (one CH 2 group present in this group or two or more non-adjacent CH 2 groups are replaced by -O- and / or -S- (May be)
(b) 1,4-phenylene group (one CH 2 group present in this group or two or more non-adjacent CH 2 groups may be replaced by -N-)
(c) 1,4-cyclohexenylene, 1,4-bicyclo (2.2.2) octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1 , 2,3,4-tetrahydronaphthalene-2,6-diyl, the group (a), the group (b) and the group (c) are substituted with CN or halogen. A is 0 or 1, and R 1 -A 1 -is the following structure,
Figure 2007204390
 (Wherein n represents 1 or 2),
Z 1 is -COO-, -OCO-, -CH 2 O-, -OCH 2- , -CH 2 CH 2- , -CH = CH-, -C≡C-,-(CH 2 ) 4 -,- CH = CH-CH 2 CH 2- , -CH 2 CH 2 -CH = CH- or a single bond,
X represents chlorine atom, bromine atom, iodine atom, trifluoromethanesulfonate, methanesulfonate, p-toluenesulfonate, boric acid, boron trifluoride, dialkylboron, trialkylsilane, mono and dialkoxysilane, mono and difluorosilane , L 1 , L 2 , L 3 and L 4 each independently represents a fluorine atom or a hydrogen atom, but at least one of L 1 , L 2 , L 3 or L 4 represents a fluorine atom). A compound of the general formula (2)
Figure 2007204390
 (In the formula, R 2 represents a hydrogen atom, an alkyl group having 1 to 15 carbon atoms, an alkyl group having 1 to 15 carbon atoms substituted by at least one halogen, an alkenyl group having 2 to 15 carbon atoms, or at least one halogen. -O- represents an alkenyl group having 2 to 15 carbon atoms substituted by the above, and one or two or more CH 2 groups present in these groups are independently defined as those in which O atoms are not directly bonded to each other. , -S-, -CO-, -COO-, -OCO- or -OCO-O- may be substituted)
(3) characterized by reacting an alcohol represented by formula (3)
Figure 2007204390
 (Wherein R 1 , A 1 , Z 1 , L 1, L 2 , L 3 , or L 4 represents the same as in general formula (1), and R 2 has the same meaning as in general formula (2) The method for producing a hydroquinone derivative represented by: 一般式(１−２)又は（１−３）General formula (1-2) or (1-3)
Figure 2007204390
Figure 2007204390
 (式中、nは1又は2を表し、Xは塩素原子、臭素原子、ヨウ素原子、トリフルオロメタンスルホネート、メタンスルホネート、p-トルエンスルホネート、ホウ酸、三フッ化ホウ素、ジアルキルホウ素、トリアルキルシラン、モノ及びジアルコキシシラン、モノ及びジフルオロシランを表し、L(Wherein n represents 1 or 2, X is a chlorine atom, bromine atom, iodine atom, trifluoromethanesulfonate, methanesulfonate, p-toluenesulfonate, boric acid, boron trifluoride, dialkylboron, trialkylsilane, Represents mono and dialkoxysilane, mono and difluorosilane, L 11 、L, L 22 、L, L 3Three 及びLAnd L 4Four はそれぞれ独立してフッ素原子又は水素原子を表すが、LEach independently represents a fluorine atom or a hydrogen atom, but L 11 、L, L 22 、L, L 3Three 又はLOr L 4Four の少なくとも一つはフッ素原子を表す)で表される化合物に、一般式(２)At least one of which represents a fluorine atom), a compound represented by the general formula (2)
Figure 2007204390
Figure 2007204390
 (式中、R(Where R 22 は、水素原子、炭素数1〜15のアルキル基、少なくとも一つのハロゲンにより置換された炭素数1〜15のアルキル基、炭素数2〜15のアルケニル基又は少なくとも一つのハロゲンにより置換された炭素数2〜15のアルケニル基を表し、これらの基中に存在する1個又は2個以上のCHIs a hydrogen atom, an alkyl group having 1 to 15 carbon atoms, an alkyl group having 1 to 15 carbon atoms substituted by at least one halogen, an alkenyl group having 2 to 15 carbon atoms or a carbon number substituted by at least one halogen. Represents 2 to 15 alkenyl groups, one or more CH present in these groups 22 基はそれぞれ独立してO原子が相互に直接結合しないものとして -O-、-S-、-CO-、-COO-、-OCO-又は-OCO-O-により置き換えられても良い)Each group may be independently replaced by -O-, -S-, -CO-, -COO-, -OCO- or -OCO-O- as if the O atoms are not directly bonded to each other)
で表されるアルコールを反応させることを特徴とする一般式(３−２)又は（３−３）Or an alcohol represented by the general formula (3-2) or (3-3)
Figure 2007204390
Figure 2007204390
 (式中、n、L(Where n, L 11 、L, L 22 、L, L 3Three 、又はLOr L 4Four は一般式（１−２）又は（１−３）のものと同じものを示し、RIs the same as that of general formula (1-2) or (1-3), and R 22 は一般式(２)と同じ意味を表す)で表されるハイドロキノン誘導体の製造方法。Represents the same meaning as in general formula (2)). 塩基性条件下に縮合反応を行う請求項１又は２記載の製造方法。 The production method according to claim 1 or 2 , wherein the condensation reaction is carried out under basic conditions. 遷移金属存在下に縮合反応を行う請求項１、２又は３記載の製造方法。 The production method according to claim 1 , 2 or 3 , wherein the condensation reaction is carried out in the presence of a transition metal.
JP2006022421A 2006-01-31 2006-01-31 Method for producing fluorine-containing liquid crystal compound having hydroquinone skeleton Expired - Fee Related JP5061466B2 (en)

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JP2007204390A5 true JP2007204390A5 (en) 2009-05-07
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JP2013155157A (en) * 2012-01-31 2013-08-15 Dic Corp Compound
CN112028748B (en) * 2020-09-14 2022-09-23 百合花集团股份有限公司 Preparation method of 2, 5-dimethoxychlorobenzene

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JPS5569536A (en) * 1978-11-17 1980-05-26 Otsuka Chem Co Ltd Preparation of alkoxyphenol derivative
JPS63280037A (en) * 1987-05-11 1988-11-17 Idemitsu Kosan Co Ltd Production of alkoxybenzenes
JPH0768519B2 (en) * 1988-11-24 1995-07-26 荒川化学工業株式会社 Liquid crystal composition
JP4654474B2 (en) * 1999-10-13 2011-03-23 チッソ株式会社 Liquid crystalline compound having branched methyl group, liquid crystal composition and liquid crystal display device
JP4691893B2 (en) * 2004-03-24 2011-06-01 Ｄｉｃ株式会社 Liquid crystal composition, display element and compound containing trifluoronaphthalene derivative.
JP4876420B2 (en) * 2005-03-31 2012-02-15 Ｄｉｃ株式会社 Difluorobenzene derivative
JP4835032B2 (en) * 2005-04-27 2011-12-14 Ｄｉｃ株式会社 Trifluoronaphthalene derivative
JP4894226B2 (en) * 2005-10-31 2012-03-14 Ｄｉｃ株式会社 Method for producing fluorine-containing liquid crystal compound having hydroquinone skeleton
JP4924863B2 (en) * 2005-10-31 2012-04-25 Ｄｉｃ株式会社 Method for producing difluorobenzene derivative

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