CN104230644A - Synthetic method of benzo-3, 4-phenanthrene - Google Patents
Synthetic method of benzo-3, 4-phenanthrene Download PDFInfo
- Publication number
- CN104230644A CN104230644A CN201410364500.3A CN201410364500A CN104230644A CN 104230644 A CN104230644 A CN 104230644A CN 201410364500 A CN201410364500 A CN 201410364500A CN 104230644 A CN104230644 A CN 104230644A
- Authority
- CN
- China
- Prior art keywords
- reaction
- add
- stirring
- organic phase
- room temperature
- 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
Abstract
The invention provides a synthetic method of benzo-3, 4-phenanthrene and belongs to the field of organic chemical synthesis. The method comprises the following steps: firstly, preparing an intermediate-A with a catalytic effect under nitrogen protection and then synthesizing an intermediate-B by virtue of the intermediate-A; adding the obtained intermediate-B and dichloromethane into a reaction flask, stirring to fully dissolve at room temperature and dropwise adding methanesulfonic acid, controlling the reaction temperature, stirring to react after dropsiwe adding and sampling and centrally controlling, then adding potassium carbonate into the reaction flask and stirring and splitting phase; respectively washing an upper layer water phase and a lower layer organic phase by pure water and saline, wherein the obtained lower layer organic phase is treated by anhydrous sodium sulfate and active carbon; and filtering, washing filter cakes by a small amount of dichloromethane, distilling under reduced pressure to obtain a crude product, adding ethyl acetate, heating to fully dissolve and slowly cooling to crystallize, and filtering, washing and drying to obtain white solid powder, wherein the yield is 61.29% and the content (HPLC) is 99.12%. Although the method is tedious in steps, the method has rules, and is easy to operate and not high in operating cost. Benzo-3, 4-phenanthrene can be put on production on a large scale.
Description
Technical field
The invention belongs to organic chemical synthesis field, relate to a kind of synthetic method of benzophenanthrene, be specifically related to a kind of synthetic method of benzo-3,4-phenanthrene.
Background technology
Benzophenanthrene, molecular formula C18H12.Molecular weight 228.30.Obtain needle-like crystal by ethanol, have carcinogenesis; Fusing point 68 DEG C, in ethanol UV λ max232,280,302,325,355,372nm; Be slightly soluble in ethanol, sherwood oil, water insoluble; The benzophenanthrene compound be made up of three phenyl ring is separate from the thermal cracking products of benzene the earliest, and is first referred to as benzophenanthrene by Schultz.Mannich has synthesized benzophenanthrene in first time in 1907, far early than the discovery of discotic mesogenic in 1977, and substantially determine its chemical structural formula, after this, the synthetic method of various benzophenanthrene and compound thereof is constantly released, until the various synthetic methods of benzophenanthrene Cheng Huan have carried out once summarizing by nineteen sixty Buess and Lawsons, and foretell that it will have special electricity or optical property.After this, the synthesis of benzophenanthrene and derivative thereof is still in continuation, and along with organic, polymer is in the breakthrough of photoelectric field, people more and more pay close attention to research and development and the synthesis of the triphenylene with special construction.
Up to the present, people have carried out a lot of research for the synthetic method of benzophenanthrene and derivative thereof, but because the molecular structure of benzophenanthrene is larger, and preparation method is too complicated, irregularities, overall cost is high, there is the limitation that running cost is too high, can not put into production in a large number.
Summary of the invention
The object of the invention is to overcome said procedure complexity, make the problem difficult, cost is high; provide a kind of synthetic method of benzo-3,4-phenanthrene, the method is under nitrogen protection; first synthetic intermediate-A; then by intermediate-A synthetic intermediate-B, benzo-3,4-is finally synthesized luxuriant and rich with fragrance; though preparation time is long; but building-up process is regular to be followed, and overall cost is not high, can put into production.
For achieving the above object, the synthetic route of benzo-3,4-phenanthrene of the present invention is:
The building-up process of benzo-3, the 4-phenanthrene that the present invention relates to comprises the following steps:
1, the synthesis of intermediate-A
(1) take 16.0g2-bromobenzaldehyde, 14.9g1-naphthalene boronic acids, 170mL toluene and 85mL ethanol respectively, under nitrogen protection, add successively in dry 500mL tetra-mouthfuls of reaction flasks, stir;
(2) after stirring, add the aqueous sodium carbonate of 92.0g20%, then add 0.5g tetrakis triphenylphosphine palladium fast, from room temperature to 78-80 DEG C (backflow), and keep at this temperature stirring, react sampling after 6 hours and carry out controlling in HPLC;
(3) control raw material 2-bromobenzaldehyde to react completely, reaction solution is cooled to 25-30 DEG C, add 40.0g water and 65.0g ethyl acetate, separate lower floor's aqueous phase, upper organic phase uses 100.0g water and 100g salt solution (sodium chloride-containing 15.0g) washing respectively, the organic phase 30.0g anhydrous sodium sulphate obtained and 3.0g activated carbon treatment, filter, collect filtrate, decompression precipitation is carried out at 65-70 DEG C, obtain 20.3g yellow oily liquid, HPLC content is 93.9%, is directly used in next step reaction.
2, the synthesis of intermediate-B
(1) measure 20.3g intermediate-A, 32.5g methoxymethyl triphenylphosphonium phosphonium chloride and 250mL tetrahydrofuran (THF) respectively, under nitrogen protection, add in 500mL tetra-mouthfuls of reaction flasks of a drying successively, stir;
(2) stir entirely molten after, slowly add 11.6g potassium tert.-butoxide, heat release is obvious, does not exceed 30 DEG C; Allow and to continue stirring after its Temperature fall to room temperature and sample after 3 hours and carry out controlling in HPLC;
(3) control raw material midbody-A to react completely, after reaction terminates, in reaction flask, add 100g water and 100ml ethyl acetate, phase-splitting after stirring 10-15min, separate lower floor's aqueous phase, upper organic phase 100.0g water and the water washing of 100.0g15% salt, the organic phase 30.0g anhydrous sodium sulphate obtained and 5.0g activated carbon treatment, filter, collect filtrate, at 65-70 DEG C, carry out decompression precipitation, obtain 37.3g safran oily liquids, HPLC content is 89.4%, is directly used in next step reaction.
3, the synthesis of the finished product
(1) measure 36.4g intermediate-B and 200mL methylene dichloride respectively, add successively under nitrogen protection in dry 250mL reaction flask, and at room temperature stir entirely molten;
(2) at room temperature dropwise 9.8g methylsulfonic acid is dripped; Control temperature of reaction between 25 ~ 30 DEG C, about 15min dropwises; Dropwise rear stirring at room temperature and react control in sampling in 10 hours;
(3), after reaction terminates, in reaction flask, the salt of wormwood of 150g10% is added, phase-splitting after stirring at room temperature 10-20min; Separate the salt water washing that upper strata aqueous phase lower floor organic phase uses 150g pure water and 150.0g15% respectively, the lower floor's organic phase anhydrous sodium sulphate obtained and activated carbon treatment; Filter, a small amount of washed with dichloromethane of filter cake, obtains light yellow liquid; Obtain 26.6g crude product through underpressure distillation, add the complete molten rear slow cooling crystallization of 30g ethyl acetate heating, filtration, washing, drying, obtain 12.1g white solid powder, yield: 61.29%, HPLC:99.12%.
The present invention is under the protection of nitrogen, first synthetic intermediate-A, then by intermediate-A synthetic intermediate-B, finally synthesizes benzo-3,4-luxuriant and rich with fragrance, though step is various, regularly to follow, simple to operation, running cost is not high, can put into production in a large number.
Embodiment:
First synthetic intermediate-A, take 16.0g2-bromobenzaldehyde, 14.9g1-naphthalene boronic acids, 170mL toluene and 85mL ethanol respectively, under nitrogen protection, add successively in dry 500mL tetra-mouthfuls of reaction flasks, after stirring, add the aqueous sodium carbonate of 92.0g20%, then 0.5g tetrakis triphenylphosphine palladium is added fast, from room temperature to 78-80 DEG C (backflow), and keep at this temperature stirring, react sampling after 6 hours and carry out controlling in HPLC; Control raw material 2-bromobenzaldehyde to react completely, reaction solution is cooled to 25-30 DEG C, adds 40.0g water and 65.0g ethyl acetate, separate lower floor's aqueous phase, upper organic phase uses 100.0g water and 100g salt solution (sodium chloride-containing 15.0g) washing respectively, the organic phase 30.0g anhydrous sodium sulphate obtained and 3.0g activated carbon treatment, filter, and collects filtrate, decompression precipitation is carried out at 65-70 DEG C, obtain 20.3g yellow oily liquid, HPLC content is 93.9%, is directly used in next step reaction; Then synthetic intermediate-B: first measure 20.3g intermediate-A, 32.5g methoxymethyl triphenylphosphonium phosphonium chloride and 250mL tetrahydrofuran (THF) respectively, under nitrogen protection, adds in 500mL tetra-mouthfuls of reaction flasks of a drying successively, stirs; Stir entirely molten after, slowly add 11.6g potassium tert.-butoxide, heat release is obvious, control temperature 30 DEG C; Allow and to continue stirring after its Temperature fall to room temperature and sample after 3 hours and carry out controlling in HPLC; Control raw material midbody-A to react completely, after reaction terminates, in reaction flask, add 100g water and 100ml ethyl acetate, phase-splitting after stirring 10-15min, separate lower floor's aqueous phase, upper organic phase 100.0g water and the water washing of 100.0g15% salt, the organic phase 30.0g anhydrous sodium sulphate obtained and 5.0g activated carbon treatment, filter, collect filtrate, at 65-70 DEG C, carry out decompression precipitation, obtain 37.3g safran oily liquids, HPLC content is 89.4%, is directly used in next step reaction; The synthesis of the finished product: first measure 36.4g intermediate-B and 200mL methylene dichloride respectively, adds successively under nitrogen protection in dry 250mL reaction flask, and at room temperature stirs entirely molten; At room temperature dropwise drip 9.8g methylsulfonic acid; Control temperature of reaction between 25 ~ 30 DEG C, about 15min dropwises; Dropwise rear stirring at room temperature and react control in sampling in 10 hours; After reaction terminates, in reaction flask, add the salt of wormwood of 150g10%, phase-splitting after stirring at room temperature 10-20min; Separate the salt water washing that upper strata aqueous phase lower floor organic phase uses 150g pure water and 150.0g15% respectively, the lower floor's organic phase anhydrous sodium sulphate obtained and activated carbon treatment; Filter, a small amount of washed with dichloromethane of filter cake, obtains light yellow liquid; Obtain 26.6g crude product through underpressure distillation, add the complete molten rear slow cooling crystallization of 30g ethyl acetate heating, filtration, washing, drying, obtain 12.1g white solid powder, yield: 61.29%, HPLC:99.12%.
Example 1
(1) first synthetic intermediate-A
Take 16.0g2-bromobenzaldehyde, 14.9g1-naphthalene boronic acids, 170mL toluene and 85mL ethanol respectively, under nitrogen protection, add in dry 500mL tetra-mouthfuls of reaction flasks successively, after stirring, add the aqueous sodium carbonate of 92.0g20%, then add 0.5g tetrakis triphenylphosphine palladium fast, from room temperature to 78-80 DEG C (backflow), and keep at this temperature stirring, react sampling after 6 hours and carry out controlling in HPLC; Control raw material 2-bromobenzaldehyde to react completely, reaction solution is cooled to 25-30 DEG C, adds 40.0g water and 65.0g ethyl acetate, separate lower floor's aqueous phase, upper organic phase uses 100.0g water and 100g salt solution (sodium chloride-containing 15.0g) washing respectively, the organic phase 30.0g anhydrous sodium sulphate obtained and 3.0g activated carbon treatment, filter, and collects filtrate, decompression precipitation is carried out at 65-70 DEG C, obtain 20.3g yellow oily liquid, HPLC content is 93.9%, is directly used in next step reaction;
(2) then synthetic intermediate-B: first measure 20.3g intermediate-A, 32.5g methoxymethyl triphenylphosphonium phosphonium chloride and 250mL tetrahydrofuran (THF) respectively, under nitrogen protection, add in 500mL tetra-mouthfuls of reaction flasks of a drying successively, stirs; Stir entirely molten after, slowly add 11.6g potassium tert.-butoxide, heat release is obvious, control temperature 30 DEG C; Allow and to continue stirring after its Temperature fall to room temperature and sample after 3 hours and carry out controlling in HPLC; Control raw material midbody-A to react completely, after reaction terminates, in reaction flask, add 100g water and 100ml ethyl acetate, phase-splitting after stirring 10-15min, separate lower floor's aqueous phase, upper organic phase 100.0g water and the water washing of 100.0g15% salt, the organic phase 30.0g anhydrous sodium sulphate obtained and 5.0g activated carbon treatment, filter, collect filtrate, at 65-70 DEG C, carry out decompression precipitation, obtain 37.3g safran oily liquids, HPLC content is 89.4%, is directly used in next step reaction;
(3) synthesis of the finished product: first measure 36.4g intermediate-B and 200mL methylene dichloride respectively, adds successively under nitrogen protection in dry 250mL reaction flask, and at room temperature stirs entirely molten; At room temperature dropwise drip 9.8g methylsulfonic acid; Control temperature of reaction at 25 DEG C, about 15min dropwises; Dropwise rear stirring at room temperature and react control in sampling in 10 hours; After reaction terminates, in reaction flask, add the salt of wormwood of 150g10%, phase-splitting after stirring at room temperature 10min; Separate the salt water washing that upper strata aqueous phase lower floor organic phase uses 150g pure water and 150.0g15% respectively, the lower floor's organic phase anhydrous sodium sulphate obtained and activated carbon treatment; Filter, a small amount of washed with dichloromethane of filter cake, obtains light yellow liquid; Obtain 26.6g crude product through underpressure distillation, add the complete molten rear slow cooling crystallization of 30g ethyl acetate heating, filtration, washing, drying, obtain 12.1g white solid powder, yield: 61.29%, HPLC:99.12%.
Example 2
(1) first synthetic intermediate-A, take 16.0g2-bromobenzaldehyde, 14.9g1-naphthalene boronic acids, 170mL toluene and 85mL ethanol respectively, under nitrogen protection, add successively in dry 500mL tetra-mouthfuls of reaction flasks, after stirring, add the aqueous sodium carbonate of 92.0g20%, then 0.5g tetrakis triphenylphosphine palladium is added fast, from room temperature to 78-80 DEG C (backflow), and keep at this temperature stirring, react sampling after 6 hours and carry out controlling in HPLC; Control raw material 2-bromobenzaldehyde to react completely, reaction solution is cooled to 25-30 DEG C, adds 40.0g water and 65.0g ethyl acetate, separate lower floor's aqueous phase, upper organic phase uses 100.0g water and 100g salt solution (sodium chloride-containing 15.0g) washing respectively, the organic phase 30.0g anhydrous sodium sulphate obtained and 3.0g activated carbon treatment, filter, and collects filtrate, decompression precipitation is carried out at 65-70 DEG C, obtain 20.3g yellow oily liquid, HPLC content is 93.9%, is directly used in next step reaction;
(2) then synthetic intermediate-B: first measure 20.3g intermediate-A, 32.5g methoxymethyl triphenylphosphonium phosphonium chloride and 250mL tetrahydrofuran (THF) respectively, under nitrogen protection, add in 500mL tetra-mouthfuls of reaction flasks of a drying successively, stirs; Stir entirely molten after, slowly add 11.6g potassium tert.-butoxide, heat release is obvious, control temperature 30 DEG C; Allow and to continue stirring after its Temperature fall to room temperature and sample after 3 hours and carry out controlling in HPLC; Control raw material midbody-A to react completely, after reaction terminates, in reaction flask, add 100g water and 100ml ethyl acetate, phase-splitting after stirring 10-15min, separate lower floor's aqueous phase, upper organic phase 100.0g water and the water washing of 100.0g15% salt, the organic phase 30.0g anhydrous sodium sulphate obtained and 5.0g activated carbon treatment, filter, collect filtrate, at 65-70 DEG C, carry out decompression precipitation, obtain 37.3g safran oily liquids, HPLC content is 89.4%, is directly used in next step reaction;
(3) synthesis of the finished product: first measure 36.4g intermediate-B and 200mL methylene dichloride respectively, adds successively under nitrogen protection in dry 250mL reaction flask, and at room temperature stirs entirely molten; At room temperature dropwise drip 9.8g methylsulfonic acid; Control temperature of reaction at 28 DEG C, about 15min dropwises; Dropwise rear stirring at room temperature and react control in sampling in 10 hours; After reaction terminates, in reaction flask, add the salt of wormwood of 150g10%, phase-splitting after stirring at room temperature 15min; Separate the salt water washing that upper strata aqueous phase lower floor organic phase uses 150g pure water and 150.0g15% respectively, the lower floor's organic phase anhydrous sodium sulphate obtained and activated carbon treatment; Filter, a small amount of washed with dichloromethane of filter cake, obtains light yellow liquid; Obtain 26.2g crude product through underpressure distillation, add the complete molten rear slow cooling crystallization of 30g ethyl acetate heating, filtration, washing, drying, obtain 12.0g white solid powder, yield: 61.25%, HPLC:99.1%.
Example 3
(1) first synthetic intermediate-A, take 16.0g2-bromobenzaldehyde, 14.9g1-naphthalene boronic acids, 170mL toluene and 85mL ethanol respectively, under nitrogen protection, add successively in dry 500mL tetra-mouthfuls of reaction flasks, after stirring, add the aqueous sodium carbonate of 92.0g20%, then 0.5g tetrakis triphenylphosphine palladium is added fast, from room temperature to 78-80 DEG C (backflow), and keep at this temperature stirring, react sampling after 6 hours and carry out controlling in HPLC; Control raw material 2-bromobenzaldehyde to react completely, reaction solution is cooled to 25-30 DEG C, adds 40.0g water and 65.0g ethyl acetate, separate lower floor's aqueous phase, upper organic phase uses 100.0g water and 100g salt solution (sodium chloride-containing 15.0g) washing respectively, the organic phase 30.0g anhydrous sodium sulphate obtained and 3.0g activated carbon treatment, filter, and collects filtrate, decompression precipitation is carried out at 65-70 DEG C, obtain 20.3g yellow oily liquid, HPLC content is 93.9%, is directly used in next step reaction;
(2) then synthetic intermediate-B: first measure 20.3g intermediate-A, 32.5g methoxymethyl triphenylphosphonium phosphonium chloride and 250mL tetrahydrofuran (THF) respectively, under nitrogen protection, add in 500mL tetra-mouthfuls of reaction flasks of a drying successively, stirs; Stir entirely molten after, slowly add 11.6g potassium tert.-butoxide, heat release is obvious, control temperature 30 DEG C; Allow and to continue stirring after its Temperature fall to room temperature and sample after 3 hours and carry out controlling in HPLC; Control raw material midbody-A to react completely, after reaction terminates, in reaction flask, add 100g water and 100ml ethyl acetate, phase-splitting after stirring 10-15min, separate lower floor's aqueous phase, upper organic phase 100.0g water and the water washing of 100.0g15% salt, the organic phase 30.0g anhydrous sodium sulphate obtained and 5.0g activated carbon treatment, filter, collect filtrate, at 65-70 DEG C, carry out decompression precipitation, obtain 37.3g safran oily liquids, HPLC content is 89.4%, is directly used in next step reaction;
(3) synthesis of the finished product: first measure 36.4g intermediate-B and 200mL methylene dichloride respectively, adds successively under nitrogen protection in dry 250mL reaction flask, and at room temperature stirs entirely molten; At room temperature dropwise drip 9.8g methylsulfonic acid; Control temperature of reaction at 30 DEG C, about 15min dropwises; Dropwise rear stirring at room temperature and react control in sampling in 10 hours; After reaction terminates, in reaction flask, add the salt of wormwood of 150g10%, phase-splitting after stirring at room temperature 20min; Separate the salt water washing that upper strata aqueous phase lower floor organic phase uses 150g pure water and 150.0g15% respectively, the lower floor's organic phase anhydrous sodium sulphate obtained and activated carbon treatment; Filter, a small amount of washed with dichloromethane of filter cake, obtains light yellow liquid; Obtain 26.0g crude product through underpressure distillation, add the complete molten rear slow cooling crystallization of 30g ethyl acetate heating, filtration, washing, drying, obtain 11.8g white solid powder, yield: 61.20%, HPLC:99.05%.
Claims (4)
1. the synthetic method of benzo-3, a 4-phenanthrene, is characterized in that: first synthesize a kind of intermediate-A and a kind of intermediate-B, then synthesize the finished product.
2. require the synthetic method of described a kind of benzo-3,4-phenanthrene according to right 1, the synthesis step of intermediate-A is:
(1) take 16.0g2-bromobenzaldehyde, 14.9g1-naphthalene boronic acids, 170mL toluene and 85mL ethanol respectively, under nitrogen protection, add successively in dry 500mL tetra-mouthfuls of reaction flasks, stir;
(2) after stirring, add the aqueous sodium carbonate of 92.0g20%, then add 0.5g tetrakis triphenylphosphine palladium fast, from room temperature to 78-80 DEG C (backflow), and keep at this temperature stirring, react sampling after 6 hours and carry out controlling in HPLC;
(3) control raw material 2-bromobenzaldehyde to react completely, reaction solution is cooled to 25-30 DEG C, add 40.0g water and 65.0g ethyl acetate, separate lower floor's aqueous phase, upper organic phase uses 100.0g water and 100g salt solution (sodium chloride-containing 15.0g) washing respectively, the organic phase 30.0g anhydrous sodium sulphate obtained and 3.0g activated carbon treatment, filter, collect filtrate, decompression precipitation is carried out at 65-70 DEG C, obtain 20.3g yellow oily liquid, HPLC content is 93.9%, is directly used in next step reaction.
3. require the synthetic method of described a kind of benzo-3,4-phenanthrene according to right 1, the synthesis step of intermediate-B is:
(1) measure 20.3g intermediate-A, 32.5g methoxymethyl triphenylphosphonium phosphonium chloride and 250mL tetrahydrofuran (THF) respectively, under nitrogen protection, add in dry 500mL tetra-mouthfuls of reaction flasks successively, stir;
(2) stir entirely molten after, slowly add 11.6g potassium tert.-butoxide, heat release is obvious, does not exceed 30 DEG C; Allow and to continue stirring after its Temperature fall to room temperature and sample after 3 hours and carry out controlling in HPLC;
(3) control raw material midbody-A to react completely, after reaction terminates, in reaction flask, add 100g water and 100ml ethyl acetate, phase-splitting after stirring 10-15min, separate lower floor's aqueous phase, upper organic phase 100.0g water and the water washing of 100.0g15% salt, the organic phase 30.0g anhydrous sodium sulphate obtained and 5.0g activated carbon treatment, filter, collect filtrate, at 65-70 DEG C, carry out decompression precipitation, obtain 37.3g safran oily liquids, HPLC content is 89.4%, is directly used in next step reaction.
4. require the synthetic method of described a kind of benzo-3,4-phenanthrene according to right 1, the synthesis step of the finished product is:
(1) measure 36.4g intermediate-B and 200mL methylene dichloride respectively, add successively under nitrogen protection in dry 250mL reaction flask, and at room temperature stir entirely molten;
(2) at room temperature dropwise 9.8g methylsulfonic acid is dripped; Control temperature of reaction between 25 ~ 30 DEG C, about 15min dropwises; Dropwise rear stirring at room temperature and react control in sampling in 10 hours;
(3), after reaction terminates, in reaction flask, the salt of wormwood of 150g10% is added, phase-splitting after stirring at room temperature 10-20min; Separate the salt water washing that upper strata aqueous phase lower floor organic phase uses 150g pure water and 150.0g15% respectively, the lower floor's organic phase anhydrous sodium sulphate obtained and activated carbon treatment; Filter, a small amount of washed with dichloromethane of filter cake, obtains light yellow liquid; Obtain 26.6g crude product through underpressure distillation, add the complete molten rear slow cooling crystallization of 30g ethyl acetate heating, filtration, washing, drying, obtain 12.1g white solid powder, yield: 61.29%, HPLC:99.12%.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410364500.3A CN104230644A (en) | 2014-07-23 | 2014-07-23 | Synthetic method of benzo-3, 4-phenanthrene |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410364500.3A CN104230644A (en) | 2014-07-23 | 2014-07-23 | Synthetic method of benzo-3, 4-phenanthrene |
Publications (1)
Publication Number | Publication Date |
---|---|
CN104230644A true CN104230644A (en) | 2014-12-24 |
Family
ID=52219661
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410364500.3A Pending CN104230644A (en) | 2014-07-23 | 2014-07-23 | Synthetic method of benzo-3, 4-phenanthrene |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104230644A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114478154A (en) * | 2022-02-25 | 2022-05-13 | 西安欧得光电材料有限公司 | Industrial synthesis method of picene |
-
2014
- 2014-07-23 CN CN201410364500.3A patent/CN104230644A/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114478154A (en) * | 2022-02-25 | 2022-05-13 | 西安欧得光电材料有限公司 | Industrial synthesis method of picene |
CN114478154B (en) * | 2022-02-25 | 2023-11-21 | 西安欧得光电材料有限公司 | Industrial synthesis method of picene |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN103497180B (en) | 4-(2,2-bis-is fluoro-1,3-benzodioxole-4-yl) synthetic method of pyrroles-3-nitrile | |
CN102060867A (en) | Method for preparing potassium trifluoroborate series compounds | |
CN102659726B (en) | Method for synthesis of dronedarone | |
CN102911022A (en) | Method for artificially synthesizing natural curcumin compound | |
CN103524320A (en) | Substituted benzophenone and preparation method thereof | |
CN105968023A (en) | Method for preparing bupropion hydrochloride | |
CN110590767B (en) | Method for synthesizing AMG837 | |
CN115784981A (en) | Preparation process of piroctone olamine salt | |
CN102050705B (en) | Novel method for preparing resveratrol through decarbonylation heck reaction | |
CN104529935B (en) | Method for synthesizing ethyl 2-(3-aldehyde-4-isobutyloxyphenyl)-4-methylthiazole-5-formate | |
CN105646285B (en) | One kind dimension Lactel sieve intermediate and its preparation method and application | |
CN104311485A (en) | Preparation method of medicine bosutinib for treating leukemia | |
CN104230644A (en) | Synthetic method of benzo-3, 4-phenanthrene | |
CN105367508B (en) | A kind of preparation method of Parecoxib Sodium synthesis technique impurity | |
CN103772189B (en) | Synthesis method of diethylstilbestrol compound methyl pigeon pea ketonic acid A | |
CN102249962B (en) | Preparation method of 1,1-disulfur-1-olefin | |
CN101519355B (en) | Method for preparing methyl dihydrojasmonate | |
CN104945434B (en) | (2 ﹣ bis- substitution phosphines phenyl) -1- alkyl-indols Phosphine ligands and its synthetic method and application | |
CN106866480A (en) | Many cyclophane selenide analog derivatives and preparation method thereof | |
CN103965041A (en) | Method for preparing 2-(4-benzyloxy phenyl)ethanol fatty acid ester | |
CN108675918B (en) | Synthesis method of piceatannol | |
CN103058884B (en) | Method for synthesizing 1-hydroxymethyl cyclopropyl acetonitrile | |
CN102993155B (en) | Preparation method of polysubstituted-diarylnaphthopyran photochromic compounds | |
CN104447178B (en) | A kind of 3, the synthetic method of 4-dibenzanthracene | |
CN104557512B (en) | A kind of 3-(bromo phenyl)-2, the preparation method of 2 '-difluoro propionic acid |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
WD01 | Invention patent application deemed withdrawn after publication | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20141224 |