JPS62226957A - Production of 2-alkoxybenzenethiol compound - Google Patents
Production of 2-alkoxybenzenethiol compoundInfo
- Publication number
- JPS62226957A JPS62226957A JP7193686A JP7193686A JPS62226957A JP S62226957 A JPS62226957 A JP S62226957A JP 7193686 A JP7193686 A JP 7193686A JP 7193686 A JP7193686 A JP 7193686A JP S62226957 A JPS62226957 A JP S62226957A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- zinc
- alkoxybenzenethiol
- alkyl group
- general formula
- 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 19
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 239000002184 metal Substances 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 229910052718 tin Inorganic materials 0.000 claims abstract description 5
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 4
- 229910052793 cadmium Inorganic materials 0.000 claims abstract description 4
- 229910052802 copper Inorganic materials 0.000 claims abstract description 4
- 229910052742 iron Inorganic materials 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 5
- 229910052745 lead Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 abstract description 16
- 239000011701 zinc Substances 0.000 abstract description 16
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract description 14
- 229920001021 polysulfide Polymers 0.000 abstract description 11
- 239000005077 polysulfide Substances 0.000 abstract description 11
- 150000008117 polysulfides Polymers 0.000 abstract description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 10
- -1 sulfide compound Chemical class 0.000 abstract description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 5
- 230000035484 reaction time Effects 0.000 abstract description 5
- 229910052749 magnesium Inorganic materials 0.000 abstract description 3
- 150000002739 metals Chemical class 0.000 abstract description 3
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000011135 tin Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000005224 alkoxybenzenes Chemical class 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- LELQMXQCPHFHED-UHFFFAOYSA-N 1-butoxy-4-(2,4,4-trimethylpentan-2-yl)benzene Chemical compound CCCCOC1=CC=C(C(C)(C)CC(C)(C)C)C=C1 LELQMXQCPHFHED-UHFFFAOYSA-N 0.000 description 1
- DCHXKQJDUGHDPB-UHFFFAOYSA-N 2-butoxy-5-(2,4,4-trimethylpentan-2-yl)benzenethiol Chemical compound CCCCOC1=CC=C(C(C)(C)CC(C)(C)C)C=C1S DCHXKQJDUGHDPB-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001802 myricyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔技術分野〕
本発明は２−アルコキシベンゼンチオール系化合物の製
造方法に関し、更に詳しくはアルコキシベンゼンのポリ
スルフィド体を出発原料として高収率に２−アルコキシ
ベンゼンチオール系化合物を製造する方法に関する。Detailed Description of the Invention [Technical Field] The present invention relates to a method for producing a 2-alkoxybenzenethiol compound, and more specifically, a method for producing a 2-alkoxybenzenethiol compound in high yield using a polysulfide of alkoxybenzene as a starting material. Relating to a method of manufacturing.
２−アルコキシベンゼンチオール系化合物は写真用カプ
ラーのバラスト成分、活性点置換成分などとして有用な
化合物である。この系の化合物については、ベンゼン誘
導体を塩化亜鉛の存在下、塩化硫黄と反応さセ高収率で
得られろポリスルフイド体を亜鉛を用いて還元し、目的
とするベンゼンチオール系化合物にすることが知られて
いる。2-Alkoxybenzenethiol compounds are useful compounds as ballast components, active point substitution components, etc. of photographic couplers. This type of compound can be obtained by reacting a benzene derivative with sulfur chloride in the presence of zinc chloride in a high yield, and reducing the polysulfide with zinc to produce the desired benzenethiol compound. Are known.
５２Ｃ１２ｚｎ ＋ ［Ｊ（”］
ＡｒＨ−ｍ−→、 Ａｒ２Ｓｘ Ａｒ５
Ｈ（Ａｒはベンゼン環、Ｘは２以上の整数を表す）しか
し上記方法では、還元に際して（通常ベルギー特許６３
５６３４号に記載の亜鉛または錫と酸の組合わせが用い
られる。）反応時間が一定でなく、反応速度をあげるた
めには多量の亜鉛と酸が必要となり、製造コストの高い
ものになってしまう。52C12zn + [J(”] ArH−m−→, Ar2Sx Ar5
H (Ar is a benzene ring, X is an integer of 2 or more) However, in the above method, during reduction (usually Belgian patent 63
The combination of zinc or tin and acid described in No. 5634 is used. ) The reaction time is not constant, and large amounts of zinc and acid are required to increase the reaction rate, resulting in high production costs.
従って、より工業化に適した２−アルコキノベンゼンチ
オール系化合物の製造方法、すなわち、反応時間が短く
、かつ安価な２−アルコキシベンゼンチオール系化合物
の合成法の開発が要望されている。Therefore, there is a need for the development of a method for producing 2-alkoxybenzenethiol compounds that is more suitable for industrialization, that is, a method for synthesizing 2-alkoxybenzenethiol compounds that requires a short reaction time and is inexpensive.
本発明の目的は、上記問題点の解決にある。すなわち、
ベンゼンポリスルフィドの還元に要する反応時間が短縮
され、安価な２−アルコキシベンゼンチオール系化合物
を得る製造方法を提供することにある。An object of the present invention is to solve the above problems. That is,
It is an object of the present invention to provide a method for producing an inexpensive 2-alkoxybenzenethiol compound in which the reaction time required for reducing benzene polysulfide is shortened.
前記本発明の目的は、下記一般式［Ｔ３で示される化合
物をＺｎならびにＭｇ 、 Ａｌ、 Ｃｏ、Ｆｅ、Ｃｄ
、ＳｎおよびＰｂから選ばれる金属の少なくとも１種の
存在下で還元して、下記一般式〔ＩＩ〕で示される２−
アルコキシベンゼンチオール系化合物を得る製造方法に
より達成された。The object of the present invention is to combine a compound represented by the following general formula [T3 with Zn, Mg, Al, Co, Fe, Cd
, Sn and Pb in the presence of at least one metal selected from the group consisting of 2-
This was achieved by a method for producing alkoxybenzenethiol compounds.
一般式ＣＩ］ 一般式〔ＩＩ〕式中、Ｒ１
はアルキル基、馬は水素原子またはアルキル基を表し、
Ｒ３はアルキル基またはアルコキシ基を表す。又は２以
上の整数を表す。General formula CI] General formula [II] In the formula, R1
represents an alkyl group, horse represents a hydrogen atom or an alkyl group,
R3 represents an alkyl group or an alkoxy group. Or represents an integer of 2 or more.
本発明において出発原料として用いられる一般式〔Ｉ〕
で示されろ２−アルコキシベンゼンポリスルフィドは、
従来公知の合成法で容易に得ることができる。General formula [I] used as a starting material in the present invention
The 2-alkoxybenzene polysulfide represented by
It can be easily obtained by conventionally known synthesis methods.
本発明は、また下記工程で示すことができる。The present invention can also be illustrated by the following steps.
一般式〔Ｉ〕および〔ＩＩ〕においてＲＩはアルキル基
を表すが、Ｒ，で表されるアルキル基として好ましくは
炭素原子数１〜３０の直鎖または分岐のアルキル基、例
えばメチル、エチル、イソプロピル、ブチル、し−ブチ
ル、オクチル、ドデシル、エイコシル、トリアコンチル
等の基を挙げることができる。Ｒ２は水素またはアルキ
ル基を表すが、Ｒ２で表されるアルキル基として好まし
くは前記Ｒ１で述べたものと同じ基を挙げることができ
る。Ｒ３はアルキル基またはアルコキシ基を表すが、Ｒ
３で表されるアルキル基としても好ましくは前記Ｒ１と
同じ基が挙げられる。Ｒ３で表されるアルコキシ基とし
て好ましくは炭素原子数１〜３ｏの直鎖または分岐のア
ルコキシ基、具体的にはメトキシ、エトキシ、プロポキ
シ、５ｅｅ−ブトキシ、オクトキシ、ドデソキシ、エイ
コツキシ、ドリアコントキシ等の基を挙げることができ
る。In general formulas [I] and [II], RI represents an alkyl group, and the alkyl group represented by R is preferably a linear or branched alkyl group having 1 to 30 carbon atoms, such as methyl, ethyl, isopropyl. , butyl, shi-butyl, octyl, dodecyl, eicosyl, triacontyl and the like. R2 represents hydrogen or an alkyl group, and the alkyl group represented by R2 is preferably the same group as described for R1 above. R3 represents an alkyl group or an alkoxy group, and R
Preferably, the alkyl group represented by 3 includes the same group as R1 above. The alkoxy group represented by R3 is preferably a linear or branched alkoxy group having 1 to 3 carbon atoms, specifically methoxy, ethoxy, propoxy, 5ee-butoxy, octoxy, dodesoxy, eicotoxy, doriacontoxy, etc. The following groups can be mentioned.
還元は亜鉛と他の金属ならびに酸（酢酸、塩酸、硫酸等
）により行われる。反応溶媒としてはベンゼン類が用い
られるが、上記酸自身が溶媒を兼ねてもよい。Reduction is carried out with zinc and other metals as well as acids (acetic acid, hydrochloric acid, sulfuric acid, etc.). Although benzenes are used as the reaction solvent, the acid itself may also serve as a solvent.
用いられる亜鉛の量は、スルフィド化合物１部当り重量
化で０．０１〜１００部、好ましくは０．１〜１０部で
ある。ここで他の金属とはＭｇ 、ｋｌｌ ｓ Ｃｕ
ｓＦｅ、 Ｃｄ、 ＳｎおよびＰｂを指し、これらは単
独で用いても２種以上が用いられてもよい。用いられる
量は、亜鉛１部当り重量比でＱ、０００１〜１部、好ま
しくは０．００１〜０．１部である。The amount of zinc used is from 0.01 to 100 parts by weight, preferably from 0.1 to 10 parts by weight per part of sulfide compound. Here, other metals include Mg, klls Cu
Refers to sFe, Cd, Sn and Pb, and these may be used alone or in combination of two or more. The amount used is Q, 0001 to 1 part by weight per part of zinc, preferably 0.001 to 0.1 part.
反応溶媒量はスルフィド化合物１部当り重量比で０．１
〜１０００部、好ましくは１〜１０部が用いられる。The amount of reaction solvent is 0.1 by weight per part of sulfide compound.
~1000 parts, preferably 1 to 10 parts are used.
本発明において一般式［ＩＩ）で示される化合物の代表
的具体例を以下に示すが、本発明はこれらに限定されな
い。In the present invention, typical examples of the compound represented by the general formula [II] are shown below, but the present invention is not limited thereto.
ＩＡ階Ｌ
ＩＴ−Ｉｎ−２
ＩＩ−３ＴＩ−”
ｎ−５ｌＴ−６
ＩＴ−７１１−８
］１ニー９Ｈ−１０
■−１１
〔実施例〕
以下に本発明の具体的実施例を記載するが、本発明はこ
れに限定されない。IA floor L IT-In-2 II-3TI-” n-5lT-6 IT-711-8 ] 1 Knee 9H-10 ■-11 [Example] Specific examples of the present invention will be described below. The present invention is not limited to this.
合成例−１〔例示化ば物ｌｌ−７の合成〕２４．４ｇの
４−ブトキシ−も−オクチルベンゼンと０．２４．９の
酸化亜鉛を２５０ ｍｌのクロロホルムに加え、還流下
に４，５ ｍｌの塩化硫黄を添加する。添加後、更に３
０分還流を続ける。反応物はクロロホルムを減圧留去し
た後、カラムクロマトグラフィで分離精製し、２６９の
ポリスルフィド体をカラメル状物質として得た。Synthesis Example-1 [Synthesis of exemplified substance 11-7] 24.4 g of 4-butoxy-octylbenzene and 0.24.9 g of zinc oxide were added to 250 ml of chloroform, and 4,5 Add ml sulfur chloride. After addition, add 3 more
Continue refluxing for 0 minutes. After chloroform was distilled off under reduced pressure, the reaction product was separated and purified by column chromatography to obtain a polysulfide of 269 as a caramel-like substance.
次に、このポリスルフィド体２４．５．９を１００罰の
トルエンに溶解し、６．５ｇの亜鉛および０．１３ｇの
鉛を加える。還流攪拌下に２４．５ｍｌの濃塩酸を添力
ｏした後、１時間反応を続ける。反応液を濾過後、トル
エンを減圧留去しカラムクロマトグラフィで分離精製し
、２３．５ ｇ（９０，９％）のオイル状目的物２−ブ
トキシ−５−ｔ−オクチルベンゼンチオールを得た。Next, this polysulfide body 24.5.9 is dissolved in 100 g of toluene and 6.5 g of zinc and 0.13 g of lead are added. After adding 24.5 ml of concentrated hydrochloric acid while stirring under reflux, the reaction was continued for 1 hour. After filtering the reaction solution, toluene was distilled off under reduced pressure and the residue was separated and purified by column chromatography to obtain 23.5 g (90.9%) of the target product in the form of an oil, 2-butoxy-5-t-octylbenzenethiol.
Ｃ＋５ＨｓｏＯ８としての元素分析値
計算値（％）Ｃニア３．４７ Ｈ：１０，２０ Ｓ
：１０．８９実測値（％）Ｃニア３．６０ Ｈ：１０
．４０ Ｓ：１０．７１合成例−２（例示化合物ｎ−
ｓの合成）２／１．４．９の４−ブトキシ−１，３−ジ
ーＬ−ブチルベンゼンと０．２０．９の亜鉛を２５０ｍ
Ｊのトルエンに加え、６０〜７０℃に加熱する。４．５
ｍｅの塩化硫黄を添加した後、加分同温度で反応させ
る。反応物はトルエンを減圧留去した後、カラムクロマ
トグラフィで分離精製し２５．５ｇのカラメル状物質で
あるポリスルフィド体を得た〇
このポリスルフィド体２４ｇを９８ ｍｌのトルエンに
溶解し、６．３ｇの亜鉛および０．１ｇの銅を加える。Elemental analysis value calculated as C+5HsoO8 (%) C near 3.47 H: 10,20 S
: 10.89 Actual value (%) C near 3.60 H: 10
．． 40 S: 10.71 Synthesis Example-2 (Exemplary Compound n-
Synthesis of s) 2/1.4.9 4-butoxy-1,3-di-L-butylbenzene and 0.20.9 zinc in 250 m
Add to toluene from J and heat to 60-70°C. 4.5
After adding me sulfur chloride, the mixture is further reacted at the same temperature. After distilling off toluene under reduced pressure, the reaction product was separated and purified by column chromatography to obtain 25.5 g of polysulfide, which is a caramel-like substance. 24 g of this polysulfide was dissolved in 98 ml of toluene, and 6.3 g of zinc was dissolved. and add 0.1 g of copper.
還流攪拌下に２４ｍ１！の濃塩酸を添加した後、１時間
反応を続ける。反応液を濾過し過剰の亜鉛を除ぎ水洗す
る。トルエンを減圧留去しカラムクロマトグラフィで分
離精製し、２２．５９ＣＢ７．３％）のオイル状目的物
２−ブトキシ−３，５−ジーＬ−プチルベンゼンチオー
ルヲ得た。24ml under reflux and stirring! After adding concentrated hydrochloric acid, the reaction is continued for 1 hour. The reaction solution is filtered to remove excess zinc and washed with water. Toluene was distilled off under reduced pressure and the residue was separated and purified by column chromatography to obtain the target product, 2-butoxy-3,5-di-L-butylbenzenethiol, in the form of an oil with a content of 22.59CB (7.3%).
Ｃ＋５ＨｓｏＯ３としての元素分析値
計算値（％）Ｃニア３．４７ Ｈ：］０．２０ Ｓ
：１０．８９実測値（％）Ｃニア３．２４ Ｈ：１０
．０３ Ｓ：１０．５５比較合成例（例示化合物Ｔｌ
−７の合成）合成例−１と同様にして合成した２−ブト
キシ−５−ｔ−オクチルベンゼン・ポリスルフィド２４
．５ｇをｉｏｏｍｅのトルエンニ溶解Ｌ ６．５ ｊｉ
ノ亜鉛を加える。還流攪拌下に２４．５ ｍｅの濃塩
酸を添加した後、３時間反応を続ける。反応液を濾過後
、トルエンを減圧留去しカラムクロマトグラフィで分離
精製し、１２．５ｇ（４８，４％）のオイル状目的物を
得た。元素分析値、ＦＤマススペクトル値より例水化合
物Ｈ−７であることが確認されたが、合成例−１に比べ
収率は約］／２に低下した。Calculated elemental analysis value as C+5HsoO3 (%) C near 3.47 H: ] 0.20 S
: 10.89 Actual value (%) C near 3.24 H: 10
．． 03 S: 10.55 Comparative synthesis example (exemplified compound Tl
Synthesis of -7) 2-Butoxy-5-t-octylbenzene polysulfide 24 synthesized in the same manner as Synthesis Example-1
．． 5g dissolved in ioome toluene L 6.5 ji
Add zinc. After adding 24.5 me of concentrated hydrochloric acid while stirring at reflux, the reaction is continued for 3 hours. After filtering the reaction solution, toluene was distilled off under reduced pressure and the product was separated and purified by column chromatography to obtain 12.5 g (48.4%) of the desired product in the form of an oil. Although it was confirmed to be Example Water Compound H-7 from the elemental analysis value and FD mass spectrum value, the yield was lowered to about ]/2 compared to Synthesis Example-1.
本発明によればアルコキシベンゼンポリスルフィド体の
還元による２−アルコキシベンゼンチオールの製造にお
いて、反応時間が短縮でき、しかも高収率カ得られ、２
−アルコキシベンゼンチオールの製造コストを大巾に低
下できる。According to the present invention, in the production of 2-alkoxybenzenethiol by reduction of an alkoxybenzene polysulfide, the reaction time can be shortened and a high yield can be obtained.
- The manufacturing cost of alkoxybenzenethiol can be significantly reduced.
Claims (1)
ｇ、Ａｌ、Ｃｕ、Ｆｅ、Ｃｄ、ＳｎおよびＰｂから選ば
れる他の金属の少なくとも１種の存在下で還元すること
を特徴とする下記一般式〔II〕で示される２−アルコキ
シベンゼンチオール系化合物の製造方法。 一般式〔 I 〕 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＿１はアルキル基、Ｒ＿２は水素またはアル
キル基を表し、Ｒ＿３はアルキル基またはアルコキシ基
を表す。Ｘは２以上の整数を表す。〕 一般式〔II〕 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＿１、Ｒ＿２およびＲ＿３は前記Ｒ＿１、Ｒ
＿２およびＲ＿３と同義である。〕[Claims] A compound represented by the following general formula [I] is
A 2-alkoxybenzenethiol compound represented by the following general formula [II], which is reduced in the presence of at least one other metal selected from g, Al, Cu, Fe, Cd, Sn and Pb. manufacturing method. General formula [I] ▲ Numerical formulas, chemical formulas, tables, etc. are available▼ [In the formula, R_1 represents an alkyl group, R_2 represents hydrogen or an alkyl group, and R_3 represents an alkyl group or an alkoxy group. X represents an integer of 2 or more. ] General formula [II] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R_1, R_2 and R_3 are the above-mentioned R_1, R
Synonymous with _2 and R_3. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7193686A JPS62226957A (en) | 1986-03-28 | 1986-03-28 | Production of 2-alkoxybenzenethiol compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7193686A JPS62226957A (en) | 1986-03-28 | 1986-03-28 | Production of 2-alkoxybenzenethiol compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62226957A true JPS62226957A (en) | 1987-10-05 |
Family
ID=13474891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7193686A Pending JPS62226957A (en) | 1986-03-28 | 1986-03-28 | Production of 2-alkoxybenzenethiol compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62226957A (en) |
-
1986
- 1986-03-28 JP JP7193686A patent/JPS62226957A/en active Pending
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