CN102329207A - Synthesis method of 2, 2'-dihydroxy-4, 4'-dimethoxybenzophenone - Google Patents
Synthesis method of 2, 2'-dihydroxy-4, 4'-dimethoxybenzophenone Download PDFInfo
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- CN102329207A CN102329207A CN201110316058A CN201110316058A CN102329207A CN 102329207 A CN102329207 A CN 102329207A CN 201110316058 A CN201110316058 A CN 201110316058A CN 201110316058 A CN201110316058 A CN 201110316058A CN 102329207 A CN102329207 A CN 102329207A
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- dimethoxybenzophenone
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- oxalyl chloride
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- SODJJEXAWOSSON-UHFFFAOYSA-N bis(2-hydroxy-4-methoxyphenyl)methanone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1O SODJJEXAWOSSON-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000001308 synthesis method Methods 0.000 title description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- 239000013067 intermediate product Substances 0.000 claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 10
- 238000001953 recrystallisation Methods 0.000 claims abstract description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000007062 hydrolysis Effects 0.000 claims abstract description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 238000000926 separation method Methods 0.000 claims abstract description 8
- 238000002390 rotary evaporation Methods 0.000 claims abstract description 7
- 239000002841 Lewis acid Substances 0.000 claims abstract description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 6
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims abstract description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000004342 Benzoyl peroxide Substances 0.000 claims abstract description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 claims abstract description 5
- 238000010189 synthetic method Methods 0.000 claims abstract description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000008096 xylene Substances 0.000 claims abstract description 4
- 229920000137 polyphosphoric acid Polymers 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000000047 product Substances 0.000 claims description 13
- -1 m-xylylene dimethyl Chemical group 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- DONPBOYMUMBGCQ-UHFFFAOYSA-N 7-oxabicyclo[3.3.1]nona-1(9),2,4-triene Chemical compound C1=CC(COC2)=CC2=C1 DONPBOYMUMBGCQ-UHFFFAOYSA-N 0.000 abstract description 2
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- 238000002329 infrared spectrum Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 description 4
- 238000010025 steaming Methods 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007036 catalytic synthesis reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
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Abstract
一种2，2’-二羟基-4，4’-二甲氧基二苯甲酮的合成方法，其方法是1、由间苯二甲醚与草酰氯在催化剂存在下，于70-80℃反应得到中间产物2，2’4，4’-四甲氧基二苯甲酮，所述的间苯二甲醚与草酰氯的物质的量的比值为1∶1-20，使用的催化剂为偶氮异丁腈或过氧化苯甲酰，用量为间苯二甲醚的质量的0.5％-2％；2、将所得中间产物与路易斯酸在有机试剂作溶剂的条件下反应，反应温度50℃，时间2-3小时，停反应后，加水水解、分液、旋蒸、重结晶，即得2，2’-二羟基-4，4’-二甲氧基二苯甲酮。所述的路易斯酸是AlCl3、ZnCl2、BF3，多聚磷酸中的一种；所述的有机试剂是二氯乙烷、甲苯、二甲苯、硝基苯、氯苯中的一种。本法反应温度适宜，催化剂简单易得、用量少，对环境污染小，更接近于绿色化学的要求。
A kind of synthetic method of 2,2'-dihydroxyl-4,4'-dimethoxybenzophenone, its method is 1, by meta-xylylene dimethyl ether and oxalyl chloride in the presence of catalyst, in 70-80 °C reaction to obtain the intermediate product 2,2'4,4'-tetramethoxybenzophenone, the ratio of the amount of m-xylylene ether to oxalyl chloride is 1:1-20, and the catalyst used It is azoisobutyronitrile or benzoyl peroxide, and the dosage is 0.5%-2% of the mass of m-phenylenediyl ether; 2. The obtained intermediate product is reacted with Lewis acid under the condition that an organic reagent is used as a solvent, and the reaction temperature is 50°C for 2-3 hours, stop the reaction, add water for hydrolysis, liquid separation, rotary evaporation, and recrystallization to obtain 2,2'-dihydroxy-4,4'-dimethoxybenzophenone. The Lewis acid is one of AlCl 3 , ZnCl 2 , BF 3 and polyphosphoric acid; the organic reagent is one of dichloroethane, toluene, xylene, nitrobenzene and chlorobenzene. The reaction temperature of this method is suitable, the catalyst is simple and easy to obtain, the dosage is small, the environmental pollution is small, and it is closer to the requirements of green chemistry.
Description
技术领域 technical field
本发明涉及到一种水溶性紫外线吸收剂的合成方法，具体是二苯甲酮类紫外线吸收2，2’-二羟基-4，4’-二甲氧基二苯甲酮的合成方法。 The invention relates to a method for synthesizing a water-soluble ultraviolet absorber, in particular to a method for synthesizing benzophenone-type ultraviolet absorbing 2,2'-dihydroxy-4,4'-dimethoxybenzophenone. the
背景技术 Background technique
二苯甲酮类化合物是一种重要的的有机中间体，它能强烈吸收紫外光，广泛应用于日用化工、医药、农药、塑料、涂料等领域。合成该类化合物的传统方法主要是光气法，但光气有剧毒，操作起来不安全，在工业化中的投资成本过高且由于它是气体，不便于运输和储存，不利于绿色化学的发展。本发明提供一种对环境污染少，且产物收率高的合成方法。 Benzophenone compounds are important organic intermediates, which can strongly absorb ultraviolet light and are widely used in daily chemical, pharmaceutical, pesticide, plastic, coating and other fields. The traditional method of synthesizing this type of compound is mainly the phosgene method, but phosgene is highly toxic, unsafe to operate, the investment cost in industrialization is too high and because it is a gas, it is not convenient for transportation and storage, which is not conducive to the development of green chemistry. develop. The invention provides a synthesis method with less environmental pollution and high product yield. the
发明内容 Contents of the invention
本发明目的旨在提供一种操作简单，反应条件温和，成本低，对环境影响小，用绿色催化剂催化合成2，2’-二羟基-4，4’-二甲氧基二苯甲酮的合成方法。 The purpose of the present invention is to provide a method of simple operation, mild reaction conditions, low cost, little impact on the environment, and catalytic synthesis of 2,2'-dihydroxy-4,4'-dimethoxybenzophenone with a green catalyst resolve resolution. the
本发明采用的技术方案如下： The technical scheme that the present invention adopts is as follows:
一种2，2’-二羟基-4，4’-二甲氧基二苯甲酮的合成方法，其方法步骤为： A kind of synthetic method of 2,2'-dihydroxyl-4,4'-dimethoxybenzophenone, its method step is:
1)、由间苯二甲醚与草酰氯在催化剂存在下，于70-80℃、反应1.5小时，得到中间产物2，2’4，4’-四甲氧基二苯甲酮，如下式(I)，所述的间苯二甲醚与草酰氯的物质的量的比值为1∶1-20，使用的催化剂为偶氮异丁腈或过氧化苯甲酰； 1), by m-xylylene dimethyl ether and oxalyl chloride in the presence of a catalyst, react at 70-80 ° C for 1.5 hours to obtain the intermediate product 2,2'4,4'-tetramethoxybenzophenone, as shown in the following formula (1), the ratio of the amount of substance of the m-phenylenedimethyl ether and oxalyl chloride is 1: 1-20, and the catalyst used is azoisobutyronitrile or benzoyl peroxide;
2)、将步骤1)所得中间产物与路易斯酸在有机试剂作溶剂的条件下反应，反应温度50℃，时间2-3小时，停反应后，加水水解、分液、旋蒸、重结晶，即得2，2’-二羟基-4，4’-二甲氧基二苯甲酮，如下式(II)； 2), react the intermediate product obtained in step 1) with the Lewis acid under the condition of an organic reagent as a solvent, the reaction temperature is 50° C., and the time is 2-3 hours. After stopping the reaction, add water for hydrolysis, liquid separation, rotary evaporation, and recrystallization. Promptly get 2,2'-dihydroxyl-4,4'-dimethoxybenzophenone, as follows formula (II);
所述的路易斯酸是AlCl3、ZnCl2、BF3，多聚磷酸中的一种；所述的有机试剂是二氯乙烷、甲苯、二甲苯、硝基苯、氯苯中的一种； The Lewis acid is one of AlCl 3 , ZnCl 2 , BF 3 , and polyphosphoric acid; the organic reagent is one of dichloroethane, toluene, xylene, nitrobenzene, and chlorobenzene;
所述的1)、2)步骤反应在惰性气体保护中进行。 Described 1), 2) step reaction is carried out under inert gas protection. the
反应方程式： Reaction equation:
本发明采用的技术方案中，步骤1)中所使用的催化剂的量为间苯二甲醚质量的0.5％-2％。 In the technical scheme adopted by the present invention, the amount of the catalyst used in step 1) is 0.5%-2% of the mass of m-phenylenedimethoxy. the
本发明采用的技术方案中，步骤1)反应后，将反应物蒸馏，直接回收草酰氯，然后直接加水水解、分液、旋蒸、重结晶，得产品2，2’-二羟基-4，4’-二甲氧基二苯甲酮。 In the technical scheme adopted by the present invention, after the reaction in step 1), the reactant is distilled, oxalyl chloride is directly recovered, and then directly added with water for hydrolysis, liquid separation, rotary steaming, and recrystallization to obtain the product 2,2'-dihydroxyl-4, 4'-Dimethoxybenzophenone. the
附图说明 Description of drawings
图1是2，2’4，4’-四甲氧基二苯甲酮的IR图 Figure 1 is the IR diagram of 2,2'4,4'-tetramethoxybenzophenone
图2是2，2’-二羟基-4，4’-二甲氧基二苯甲酮的IR图 Figure 2 is the IR diagram of 2,2'-dihydroxy-4,4'-dimethoxybenzophenone
具体实施方式 Detailed ways
以下通过具体实施例来说明本发明，但本发明的保护范围不限于此。 The present invention is illustrated by specific examples below, but the protection scope of the present invention is not limited thereto. the
实施例1 Example 1
2，2’-二羟基-4，4’-二甲氧基二苯甲酮合成，其操作步骤如下： 2,2'-dihydroxy-4,4'-dimethoxybenzophenone synthesis, the operation steps are as follows:
第一步反应：取13.8g间苯二甲醚置于三口烧瓶中，加入0.15g偶氮异丁腈作催化剂，加磁子并搭建好装置；向烧瓶中加入30ml草酰氯，调节好温度并搅拌；控制温度在70-80℃、反应1.5小时；停反应，加水水解草酰氯，过滤收集中间产物并烘干，中间产物2，2’4，4’-四甲氧基二苯甲酮红外图谱如图1，1HNMR(400MHz，DMSO-d6)δ：7.35-7.30(m，2H)，6.56(s，4H)，3.81(s，6H)，3.58(s，6H)； The first step reaction: take 13.8g m-xylylene dimethyl ether and place it in a three-necked flask, add 0.15g azoisobutyronitrile as a catalyst, add a magnet and build the device; add 30ml oxalyl chloride to the flask, adjust the temperature and Stir; control the temperature at 70-80°C, react for 1.5 hours; stop the reaction, add water to hydrolyze oxalyl chloride, filter and collect the intermediate product and dry it, the intermediate product 2,2'4,4'-tetramethoxybenzophenone infrared Spectrum as shown in Figure 1, 1 HNMR (400MHz, DMSO-d6) δ: 7.35-7.30 (m, 2H), 6.56 (s, 4H), 3.81 (s, 6H), 3.58 (s, 6H);
第二步反应：将30g AlCl3和第一步中间产物置于烧瓶中，再加入100ml二氯乙烷，搅拌，控温；控制温度在50℃，时间2-3小时；停反应后，加水水解、分液、旋蒸、重结晶，得产品2，2’-二羟基-4，4’-二甲氧基二苯甲酮。HPLC检测含量为99.2％，收率72％。产物2，2’-二羟基-4，4’-二甲氧基二苯甲酮的红外图谱如图2，1HNMR(400MHz，CDCl3)δ：11.33(s，2H)，6.55-6.53(m，2H)，6.50-6.45(m，4H)，3.67(s，6H)。 The second step reaction: put 30g AlCl 3 and the intermediate product of the first step in a flask, then add 100ml dichloroethane, stir, and control the temperature; control the temperature at 50°C for 2-3 hours; after stopping the reaction, add water Hydrolysis, liquid separation, rotary steaming, and recrystallization give the product 2,2'-dihydroxy-4,4'-dimethoxybenzophenone. The content detected by HPLC was 99.2%, and the yield was 72%. The infrared spectrum of the product 2,2'-dihydroxy-4,4'-dimethoxybenzophenone is shown in Figure 2, 1 HNMR (400MHz, CDCl 3 ) δ: 11.33(s, 2H), 6.55-6.53( m, 2H), 6.50-6.45 (m, 4H), 3.67 (s, 6H).
实施例2 Example 2
第一步反应；取13.8g间苯二甲醚置于三口烧瓶中，加入0.16g偶氮异丁腈催化剂，加磁子并搭建好装置；向烧瓶中加入30ml草酰氯，调节好温度并搅拌；控制温度在70-80℃、反应1.5小时；停反应，加水水解草酰氯，过滤收集中间产物并烘干；中间产物2，2’4，4’-四甲 氧基二苯甲酮红外图谱如图1； The first step of reaction: take 13.8g of m-phenylenedimethyl ether and place it in a three-necked flask, add 0.16g of azoisobutyronitrile catalyst, add a magnet and build the device; add 30ml of oxalyl chloride into the flask, adjust the temperature and stir ; Control the temperature at 70-80 ° C, react for 1.5 hours; stop the reaction, add water to hydrolyze oxalyl chloride, filter and collect the intermediate product and dry it; the infrared spectrum of the intermediate product 2,2'4,4'-tetramethoxybenzophenone Figure 1;
第二步反应：将30g ZnCl2和第一步中间产物置于烧瓶中，再加入100ml二氯乙烷，搅拌，控温；控制温度在50℃左右，时间2-3小时；停反应后，加水水解、分液、旋蒸、重结晶，得产品2，2’-二羟基-4，4’-二甲氧基二苯甲酮，HPLC检测含量为99.1％，收率70％。产物2，2’-二羟基-4，4’-二甲氧基二苯甲酮的红外图谱如图2。 The second step reaction: put 30g ZnCl 2 and the intermediate product of the first step in a flask, then add 100ml dichloroethane, stir, and control the temperature; control the temperature at about 50°C for 2-3 hours; after stopping the reaction, Add water for hydrolysis, liquid separation, rotary steaming, and recrystallization to obtain the product 2,2'-dihydroxy-4,4'-dimethoxybenzophenone. The content detected by HPLC is 99.1%, and the yield is 70%. The infrared spectrum of the product 2,2'-dihydroxy-4,4'-dimethoxybenzophenone is shown in Figure 2.
实施例3 Example 3
第一步反应：取13.8g间苯二甲醚置于三口烧瓶中，加入0.14g偶氮异丁腈催化剂，加磁子并搭建好装置；向烧瓶中加入30ml草酰氯，调节好温度并搅拌；控制温度在70-80℃、反应1.5小时；停反应，加水水解草酰氯，过滤收集中间产物并烘干；中间产物2，2’4，4’-四甲氧基二苯甲酮红外图谱如图1； The first step reaction: take 13.8g of m-phenylenedimethyl ether and put it in a three-necked flask, add 0.14g of azoisobutyronitrile catalyst, add a magnet and build the device; add 30ml of oxalyl chloride into the flask, adjust the temperature and stir ; Control the temperature at 70-80°C, react for 1.5 hours; stop the reaction, add water to hydrolyze oxalyl chloride, filter and collect the intermediate product and dry it; the infrared spectrum of the intermediate product 2,2'4,4'-tetramethoxybenzophenone Figure 1;
第二步反应：将30g AlCl3和第一步中间产物置于烧瓶中，再加入100ml氯苯，搅拌，控温：控制温度在50℃，时间2-3小时；停反应后，加水水解、分液、旋蒸、重结晶，得产品2，2’-二羟基-4，4’-二甲氧基二苯甲酮，HPLC检测含量为99.0％，收率67％。产物2，2’-二羟基-4，4’-二甲氧基二苯甲酮的红外图谱如图2。 The second step reaction: put 30g AlCl 3 and the first step intermediate product in a flask, then add 100ml chlorobenzene, stir, and temperature control: control the temperature at 50°C for 2-3 hours; after stopping the reaction, add water for hydrolysis, Liquid separation, rotary evaporation, and recrystallization gave the product 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, the HPLC detection content was 99.0%, and the yield was 67%. The infrared spectrum of the product 2,2'-dihydroxy-4,4'-dimethoxybenzophenone is shown in Figure 2.
实施例4 Example 4
第一步反应：取13.8g间苯二甲醚置于三口烧瓶中，加入0.15g过氧化苯甲酰催化剂，加磁子并搭建好装置；向烧瓶中加入30ml草酰氯，调节好温度并搅拌；控制温度在70-80℃、反应1.5小时；停反应，加水水解草酰氯，过滤收集中间产物并烘干；中间产物2，2’4，4’-四甲氧基二苯甲酮红外图谱如图1； The first step reaction: take 13.8g of m-phenylenedimethyl ether and put it in a three-necked flask, add 0.15g of benzoyl peroxide catalyst, add a magnet and build the device; add 30ml of oxalyl chloride into the flask, adjust the temperature and stir ; Control the temperature at 70-80°C, react for 1.5 hours; stop the reaction, add water to hydrolyze oxalyl chloride, filter and collect the intermediate product and dry it; the infrared spectrum of the intermediate product 2,2'4,4'-tetramethoxybenzophenone Figure 1;
第二步反应：将30g AlCl3和第一步中间产物置于烧瓶中，再加入100m甲苯，搅拌，控温；控制温度在50℃，时间2-3小时；停反应后，加水水解、分液、旋蒸、重结晶，得产品2，2’-二羟基-4，4’-二甲氧基二苯甲酮，HPLC检测含量为99.0％，收率69％。产物2，2’-二羟基-4，4’-二甲氧基二苯甲酮的红外图谱如图2。 The second step reaction: put 30g AlCl 3 and the intermediate product of the first step in a flask, then add 100m toluene, stir, and control the temperature; control the temperature at 50°C for 2-3 hours; after stopping the reaction, add water to hydrolyze and separate solution, rotary evaporation, and recrystallization to obtain the product 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, the content detected by HPLC was 99.0%, and the yield was 69%. The infrared spectrum of the product 2,2'-dihydroxy-4,4'-dimethoxybenzophenone is shown in Figure 2.
实施例5 Example 5
第一步反应：取13.8g间苯二甲醚置于三口烧瓶中，加入0.16g过氧化苯甲酰催化剂，加磁子并搭建好装置；向烧瓶中加入30ml草酰氯，调节好温度并搅拌；控制温度在70-80℃、反应1.5小时；停反应，加水水解草酰氯，过滤收集中间产物并烘干；中间产物2，2’4，4’-四甲氧基二苯甲酮红外图谱如图1； The first step reaction: take 13.8g of m-xylylene ether in a three-necked flask, add 0.16g of benzoyl peroxide catalyst, add a magnet and build the device; add 30ml of oxalyl chloride into the flask, adjust the temperature and stir ; Control the temperature at 70-80°C, react for 1.5 hours; stop the reaction, add water to hydrolyze oxalyl chloride, filter and collect the intermediate product and dry it; the infrared spectrum of the intermediate product 2,2'4,4'-tetramethoxybenzophenone Figure 1;
第二步反应：将10gBF3和第一步中间产物置于烧瓶中，再加入100ml二甲苯，搅拌，控温；控制温度在50℃，时间2-3小时；停反应后，加水水解、分液、旋蒸、重结晶，得产品2，2’- 二羟基-4，4’-二甲氧基二苯甲酮，HPLC检测含量为99.1％，收率71％。产物2，2’-二羟基-4，4’-二甲氧基二苯甲酮的红外图谱如图2。 The second-step reaction: put 10g of BF 3 and the intermediate product of the first step in a flask, then add 100ml of xylene, stir, and control the temperature; control the temperature at 50°C for 2-3 hours; after stopping the reaction, add water to hydrolyze and separate solution, rotary evaporation, and recrystallization to obtain the product 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, the content detected by HPLC was 99.1%, and the yield was 71%. The infrared spectrum of the product 2,2'-dihydroxy-4,4'-dimethoxybenzophenone is shown in Figure 2.
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| CN103467268A (en) * | 2013-09-26 | 2013-12-25 | 山东午阳化工股份有限公司 | Preparation method of 2,2'- dyhydroxyl-4,4'-dimethoxybenzophenone |
| CN104292136A (en) * | 2014-09-19 | 2015-01-21 | 浙江科技学院 | Preparation method of sulfogaiacol |
| CN116253638A (en) * | 2023-02-08 | 2023-06-13 | 重庆长风化学工业有限公司 | Method for synthesizing 2, 4-dimethoxy benzoyl chloride and 2, 4-dimethoxy benzoic acid |
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| CN1181376A (en) * | 1996-11-01 | 1998-05-13 | 武田药品工业株式会社 | Production of benzophenone derivatives |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103467268A (en) * | 2013-09-26 | 2013-12-25 | 山东午阳化工股份有限公司 | Preparation method of 2,2'- dyhydroxyl-4,4'-dimethoxybenzophenone |
| CN103467268B (en) * | 2013-09-26 | 2015-03-25 | 山东午阳化工股份有限公司 | Preparation method of 2,2'- dyhydroxyl-4,4'-dimethoxybenzophenone |
| CN104292136A (en) * | 2014-09-19 | 2015-01-21 | 浙江科技学院 | Preparation method of sulfogaiacol |
| CN104292136B (en) * | 2014-09-19 | 2016-03-09 | 浙江科技学院 | A kind of preparation method of thiocol |
| CN116253638A (en) * | 2023-02-08 | 2023-06-13 | 重庆长风化学工业有限公司 | Method for synthesizing 2, 4-dimethoxy benzoyl chloride and 2, 4-dimethoxy benzoic acid |
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