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CAS No. : | 123-01-3 | MDL No. : | MFCD00008974 |
Formula : | C18H30 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KWKXNDCHNDYVRT-UHFFFAOYSA-N |
M.W : | 246.43 | Pubchem ID : | 31237 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | Stage #1: maleic anhydride; 1-dodecylbenzene With Aluminum Chloride In dichloromethane at 20℃; Stage #2: With hydrogenchloride In dichloromethane; water monomer Cooling with ice; | 4.1.1. Synthesis General procedure: Compounds (1-27) are synthesized as described in literature [25], by Friedel-Crafts acylation of substituted benzenes with maleic acid anhydride using anhydrous AlCl3 as the catalyst in dry CH2Cl2. The 6.125 g (62.5 mmol) of maleic acid anhydride, 16.5 g (125 mmol) of anhydrous AlCl3 and 62.5 mmol of aromatic substrates were used. After 4-6 h of stirring on room temperature the reaction mixture was captured with ice/conc. HCl. The solvent was removed by steam distillation. The residuals was filtered on vacuum, or extracted by appropriate solvent. In this way obtained solids or oily substances are processed by solution of Na2CO3 to pH 8.5, filtered to remove traces of Al from catalyst, neutralized by dropwise addition of conc. HCl, filtered, than washed thoroughly by water, dried and crystallized from appropriate solvent. Yields of pure products were from 40 to 92%. |
75% | With Aluminum Chloride In dichloromethane at 0 - 20℃; for 2h; | |
With carbon disulfide; aluminium chloride anhydrous |
With aluminium chloride anhydrous In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Stage #1: succinic acid anhydride With aluminum (III) chloride In octane at 25℃; for 0.166667h; Stage #2: 1-dodecylbenzene In octane at 25℃; for 0.5h; | 2 Example 2 Synthesis of 4-dodecylphenyl-4-oxobutanoic acid a) Add 23g of succinic anhydride and 100g of octane to a 500mL single-necked flask, quickly add 70g of anhydrous aluminum trichloride, mix and stir evenly, keep the reaction temperature at 25°C, and react for 10 minutes to obtain a mixed solution;b) Add 40 g of dodecylbenzene to the mixed solution, continue the reaction, keep the reaction temperature at 25°C, and react for 30 minutes to obtain a reaction solution;c) Slowly add 400 mL of deionized water to the reaction solution and stir, after standing still, it is separated into an oil phase and a water phase, and the oil phase is separated;d) Distilling the oil phase under reduced pressure at 95°C to obtain the product 4-dodecylphenyl-4-oxobutanoic acid.After acid-base titration and nuclear magnetic resonance detection, the structure of 4-dodecylphenyl-4-oxobutyric acid prepared in Example 2 of the present invention is: The purity of 4-dodecylphenyl-4-oxobutyric acid prepared in Example 2 of the present invention reached 96%, and the yield reached 94%. |
64% | With aluminium trichloride In carbon disulfide at 0 - 20℃; | |
55% | With aluminium trichloride In nitrobenzene for 1h; Ambient temperature; |
With aluminium trichloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | In chloroform for 5h; Reflux; | A.1 The synthesis of 2-(4-dodecyl-benzoyl)-benzoic acid is performed by reacting 45.0 g of dodecylbenzene and 29.8 g of phtalic acid anhydride in a Friedel-Crafts reaction in the presence of 500 ml of chloroform. Upon the addition of 58.5 g of AlCl3 to the mixture of the educts, a slight exotherme is observed, followed by an evolvement of HCl gas for 1.5 hours. After the gas formation has ceased, the reaction mixture is brought to boiling until gas formation is observed again, and refluxed for another 5 hours until no more HCl gas forms. After being cooled to room temperature, the reaction mass is poured in to 300 ml of water, acidified with HCl and filtered. The crude product is washed with water until a pH of seven is reached. 2-(4-Dodecyl-benzoyl)-benzoic acid is obtained as a white crystalline solid.Melting point: 85° C. (Yield: 48%)NMR analysis confirms the general structure (evidence for the presence of isomers). |
With carbon disulfide; aluminium trichloride | ||
With aluminium trichloride In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; sulfur trioxide | ||
With sulfuric acid; sulfur trioxide | ||
With sulfuric acid at 55℃; for 2h; Yield given; |
With chlorosulfonic acid In 1,2-dichloro-ethane at 20℃; | ||
With sulfur dioxide; sulfur trioxide | ||
With sulfuric acid; sulfur trioxide at 35 - 50℃; for 3h; | 1 Sulfonation of LAB was carried out as follow: 1.5 mole of fuming sulfuric acid containing (7-8% sulfur triox- ide) was added drop wise to 1 mole of LAB with vigorous stirring to avoid foaming. After complete addition, the reaction tempera- ture is kept at 35-50 °C for 3 hrs. Then the reaction mixture was cooled to ambient temperature and poured slowly into a separat- ing funnel containing concentrated HCl mixed with crushed ice. Then the mixture was shaken for 15 min and linear alkyl benzene sulphonic acid (LABSA) was extracted from aqueous layer dissolved with diethyl ether. Ether extracts was then evaporated in a rotary evaporator. (LABSA) was obtained as a dark brown liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium on activated charcoal; ethanol Hydrogenolyse; | ||
With copper-zinc-aluminium oxide at 165 - 175℃; Hydrogenolyse; | ||
With sodium ethanolate; hydrazine hydrate at 180℃; |
With hydrogenchloride; amalgamated zinc | ||
With copper oxide-chromium oxide at 165℃; Hydrogenation; | ||
With potassium hydroxide; hydrazine hydrate; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol at 135℃; | ||
With potassium hydroxide; hydrazine | ||
With hydrazine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminium trichloride | ||
at 80℃; | 3 EXAMPLE 3; An excess of benzene is created with bromo-1 dodecane in a flask that is topped with a coolant. Aluminum chloride (AlCl3) is added to the mixture. This mixture is heated to 80° C. while being stirred. The products of the reaction are, on the one hand, unreacted benzene, because it is in excess, and, on the other hand, phenyl-I dodecane (R1=R2=H, R3=normal dodecyl). The benzene is eliminated by distillation. The cetane number of the product that is finally obtained is 68 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In carbon disulfide 0 deg C, 1 h, RT, 2 h; | |
95% | With aluminum (III) chloride In dichloromethane at 0℃; for 1h; | |
78% | With aluminium trichloride In dichloromethane at -5 - 20℃; for 5h; |
54% | With aluminium trichloride at 50℃; for 1h; | |
With aluminium trichloride | ||
With aluminium trichloride at -20℃; | ||
With tetrachloromethane; aluminium trichloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With aluminium trichloride In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With lithium aluminium tetrahydride In tetrahydrofuran at 60℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With aluminium trichloride In dichloromethane at 0℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With aluminium trichloride In carbon disulfide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In diethyl ether at -25℃; | |
82% | In diethyl ether at -25℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With trifluoroacetic acid at 80℃; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With aluminium trichloride In carbon disulfide at 40℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With aluminium trichloride In dichloromethane; nitrobenzene for 1h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With iron(III) chloride In dichloromethane at 0℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With aluminium trichloride In dichloromethane at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; tetrabutyl ammonium fluoride; palladium(II) bromide In tetrahydrofuran at 20℃; for 14h; | |
88% | With di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; tetrabutyl ammonium fluoride; palladium(II) bromide In tetrahydrofuran at 20℃; for 14h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Me(C5H3)(CH2)4SO2Cl(1+)*CF3SO3(1-); scandium tris(trifluoromethanesulfonate) at 80℃; for 24h; | ||
With commercial Beta-2 zeolite catalyst In decane at 120℃; Inert atmosphere; | 3.3.1 Alkylation Alkylation of 1-dodecene (Acros, 93-95%) was performed in a 60mL reactor that was loaded under N2 atmosphere with 100mg dried catalyst, 8.4mL benzene, 21.1mL n-decane (Acros, 99%), and 2.4mL 1-dodecene (molar ratio benzene:1-dodecene 20), pressurized with 30barN2, and heated to 120°C with stirring speed 1250rpm. | |
With aluminum (III) chloride; water; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide at 35 - 80℃; |
With methanesulfonic acid at 60℃; for 5.5h; Inert atmosphere; | 1 Example 1 To produce dodecylbenzene with 100% methanesulfonic acid as catalyst, 164 g of benzene, 50 g of 1-dodecene and 283 g of n-octane together with 769 g of methanesulfonic acid (Lutropur 100 from BASF SE) were charged into a double-walled glass reactor of 2.5 l in volume. The glass reactor was provided with a stirrer, a condenser and a thermocouple. The experiment was performed under an argon inert gas atmosphere. After stirring the solution for 2 minutes at 1000 rpm the stirrer was stopped. A phase separation occurred within about 120 seconds. Once the phases had separated, a start sample of the organic phase was taken. The reaction mixture was subsequently heated to 60° C. over 30 minutes with stirring at 1000 rpm and then stirred for a further five hours at this temperature. After each hour the stirrer was briefly stopped and, after phase separation, a sample of the organic phase was taken. Once reaction had ended the stirrer was stopped and the reaction mixture was cooled to room temperature. This caused the phases to separate. The upper hydrophobic phase was clear and colorless. The lower, methanesulfonic acid-containing phase exhibited slight brown discoloration. This phase was drained off. This affords 428 g of hydrophobic phase and 777 g of hydrophilic, methanesulfonic acid-containing phase. The samples of organic phase were analyzed by gas chromatography to monitor the progress of the reaction. The decline in the dodecene concentration and the formation of dodecylbenzene isomers were observed. The areas of the GC signals for the dodecene isomers, for the dodecylbenzene isomers and for n-octane were measured and the dodecene isomers/octane and dodecylbenzene isomers/octane ratios were calculated. To observe the decline in the dodecene concentration, concentrations were normalized to the value of the start sample. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With palladium diacetate; potassium <i>tert</i>-butylate; 1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane In 1,4-dioxane at 20℃; for 26h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With palladium diacetate; potassium <i>tert</i>-butylate; 1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane In 1,4-dioxane at 90℃; for 29h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminium trichloride In dichloromethane at 20℃; for 5h; | ||
With carbon disulfide at 50℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.23 g | Stage #1: 1-dodecylbenzene With iodine; acetic acid; periodic acid at 80℃; for 3h; Stage #2: 3,9-dichloroindolo[3,2-b]carbazole With 18-crown-6 ether; potassium carbonate; 1,2-dichloro-benzene for 24h; Heating; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3% | With hydrogen; 1-butyl-3-methylimidazolium Tetrafluoroborate at 90℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodine; acetic acid; periodic acid at 80℃; for 3h; Title compound not separated from byproducts.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 1,8-diazabicyclo[2.2.2.]octane In tetrahydrofuran; diethyl ether; toluene at 25℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: AlCl3 / CH2Cl2 / 5 h / 20 °C 2: NaBH4 / methanol / 2 h / 20 °C 3: 92 percent / p-toluenesulfonic acid monohydrate / toluene / 2 h / Heating | ||
Multi-step reaction with 3 steps 1: aluminum (III) chloride / dichloromethane / 1 h / 0 °C 2: sodium tetrahydroborate / ethanol / 1.5 h / Reflux 3: toluene-4-sulfonic acid / toluene / 2 h / Dean-Stark; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 90 percent / AlCl3 / CS2 / Heating 2: aq. NaOH / acetone / 0.25 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: AlCl3 / CH2Cl2 2: 63 percent / NaOH / H2O | ||
Multi-step reaction with 2 steps 1: AlCl3 2: dioxane; aqueous NaBrO | ||
Multi-step reaction with 2 steps 1: aluminium chloride; carbon disulfide 2: aqueous sodium hypobromite solution |
Multi-step reaction with 2 steps 1: AlCl3 | ||
Multi-step reaction with 2 steps 1: carbon disulfide / 50 °C 2: sodium hypobromide / tetrahydrofuran / 3 h / 0 - 5 °C / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; methy ether; dichloromethane | P.1.1 (1) (1) Synthesis of p-n-Dodecylbenzaldehyde To 70 mL of dehydrated dichloromethane, 24.68 g (100 mmol) of n-dodecylbenzene was added and 36.82 g (189 mmol) of titanium tetrachloride was gradually added in drops. The reaction system kept below 10° C. in an ice bath and 13.16 9 (114 mmol) of 1,1-dichloromethl methy ether added in drops thereto were stirred together below 10° C. for 30 minutes and further stirred at a room temperature for 45 minutes. The resultant reaction mixture was added to 500 mL of ice water. It was extracted four times with 200 mL of dichloromethane and dried overnight on sodium sulfate. The solvent was removed by the use of an evaporator and purified by column chromatography (silica gel, benzene:hexene =1:1). Consequently, 11.22 g (40.2 mmol) of a light yellow slightly viscous liquid was obtained. The yield was 40%. 1H-NMR (500 MHz CDCl3) 0.88 (t, J=7.0 Hz, 3H, -CH2(CH2)10CH), 1.31-1.23 (m, 18H, -(CH2)2(CH2)9CH3), 1.64 (quintet, J=7.4 Hz, 2H, -CH2CH2C10H21), 2.68 (t, J=7.8 Hz, 2H, -Ar-CH2CH11H23), 7.33 (d, J=8.0 Hz, 2H, meta Ar), 7.79 (d, J=8.5 Hz, 2H, ortho Ar), 9.97 (s, 1H, -CHO). |
Multi-step reaction with 2 steps 1: tin (IV)-chloride; carbon disulfide 2: propan-1-ol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; water; ethyl acetate | 3 Preparation of 2,5-Bis(4-dodecylbenzoyl)terephthalic Acid Preparation of 2,5-Bis(4-dodecylbenzoyl)terephthalic Acid To a mixture of 492 grams of aluminum chloride and 988 mL of 1,2-dichloroethane was added 192 grams of benzene-1,2,4,5-tetracarboxylic acid dianhydride (pyromellitic dianhydride). The resulting mixture was cooled to 16° C. and a solution of 434 grams of 1-dodecylbenzene, 123 grams of diisopropylethylamine and 480 mL of 1,2-dichloroethane was added over a period of 3.5 hours, keeping the temperature between 15° C. and 20° C. during the addition. The mixture was stirred overnight at room temperature and poured into a beaker of 1000 grams of ice and 1000 grams concentrated hydrochloric acid. The mixture was stirred for one hour and the liquid was poured from the coagulate. The mixture was divided into 800 mL portions and each portion was worked up as follows. To 800 mL of the mixture was added 800 mL of tetrahydrofuran, 800 mL of ethyl acetate, and 800 mL of water. The mixture was stirred and phase split. The organic phase was filtered and the filtrate was concentrated in vacuo. The residues were combined. To 127 grams of the combined residue was added 800 mL of ethyl acetate and the mixture was stirred until a suspension of a fine solid resulted. The solid was collected by filtration and washed with 50 mL of ethyl acetate. The solid was dried to give 2,5-bis(4-dodecylbenzoyl)terephthalic acid. | |
With hydrogenchloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; water; ethyl acetate | 5 Preparation of 2,5-Bis(4-dodecylbenzoyl)terephthalic Acid Preparation of 2,5-Bis(4-dodecylbenzoyl)terephthalic Acid To a mixture of 492 grams of aluminum chloride and 988 mL of 1,2-dichloroethane was added 192 grams of benzene-1,2,4,5-tetracarboxylic acid dianhydride (pyromellitic dianhydride). The resulting mixture was cooled to 16° C. and a solution of 434 grams of 1-dodecylbenzene, 123 grams of diisopropylethylamine and 480 mL of 1,2-dichloroethane was added over a period of 3.5 hours, keeping the temperature between 15° C. and 20° C. during the addition. The mixture was stirred overnight at room temperature and poured into a beaker of 1000 grams of ice and 1000 grams concentrated hydrochloric acid. The mixture was stirred for one hour and the liquid was poured from the coagulate. The mixture was divided into 800 mL portions and each portion was worked up as follows. To 800 mL of the mixture was added 800 mL of tetrahydrofuran, 800 mL of ethyl acetate and 800 mL of water. The mixture was stirred and phase split. The organic phase was filtered and the filtrate was concentrated in vacuo. The resulting residues were combined. To 127 grams of the combined residue was added 800 mL of ethyl acetate and the resulting mixture was stirred until a suspension of a fine solid resulted. The solid was collected by filtration and washed with 50 mL of ethyl acetate. The solid was dried to give 2,5-bis(4-dodecylbenzoyl)terephthalic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | With potassium iodate; trifluorormethanesulfonic acid; acetic anhydride In carbon dioxide; water | 3 Example 3 Example 3 - Preparation of Di(dodecylphenyl)iodonium Trifluoromethanesulfonate. Into a 250 ml 3-neck round bottom flask equipped with a mechanical stirrer, thermometer, and inlet was charged, with agitation, 8.67 grams (40.6 mmol, 0.5 eq) of potassium iodate, 20.0 grams (18.2 mmol, 1.0 eq) of dodecylbenzene, and 40 mL of acetic anhydride to form a mixture. To the mixture was added 12.2 grams (7.19 mL, 81.2 mmol, 1.0 eq) of triflic acid at 0° C. dropwise at such a rate that the reaction temperature did not exceed 0° C. The reaction mixture was allowed to slowly warm to room temperature over about a 14 hour period and then quenched with 20 mL of water at 0° C. while agitation continued. The mixture was extracted with methylene chloride and the methylene chloride layer was washed with sodium bicarbonate until neutral. The methylene chloride layer was concentrated in vacuo and slowly began to thicken. This material was dissolved in approximately 600 mL of hexanes and cooled in dry ice. A precipitate formed and the mixture was filtered and washed with cold hexanes. The precipitate was collected to give 4.9 grams of a waxy flaky solid (13% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | 7 EXAMPLE 7 From the results of the analysis of the solid, it was confirmed that 4-dodecylphenylsulfonyl fluoride was formed in a yield of 30% based on dodecylbenzene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With carbon disulfide | 1.A A. A. p-Dodecylphenacyl chloride In accordance with the procedure in Org. Syn., Coll. Vol. 3, page 183, carbon disulfide (225 ml) chloroacetyl chloride (0.35 mole) and dodecylbenzene (0.2 mole) were placed in a 1-liter, 3-neck flask fitted with a mechanical strirrer, 2 condensers in series with a drying tube and a 125-ml. flask (containing aluminum chloride) attached by tubing. Six tenths of a mole (80 g) of aluminum chloride was added portionwise, with vigorous stirring, over a half-hour period. After the addition of AlCl3 was completed, the reaction mixture was refluxed for 45 minutes and permitted to stand overnight. After the overnight period, the remaining AlCl3 was decomposed with hydrochloric acid and the product was worked up in a organic phase ("Skelly B"), separated, washed, dried, and isolated as a dark green oil. Nuclear magnetic resonance (NMR) and infrared (IR) confirmed the product as p-dodecylphenacyl chloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | 30 EXAMPLE 30 EXAMPLE 30 100.8 g (1.2 mols) of diketene were added dropwise at -30°C to 0.5 1 of anhydrous hydrofluoric acid and a mixture of 0.6 mol of tetrahydronaphthalene and 0.6 mol of commercial grade dodecyl-benzene were dropped in. After stirring for 12 hours at room temperature, the reaction mixture was stirred into 3 1 of icewater. After extraction with methylene chloride, wahing with water to remove the acid from the organic phase and distillation of the methylene chloride, distillation of the reaction yielded 86 % of acetoacetyl-tetrahydronaphthalene boiling at 135°C under 0.5 torr and 77 g |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With hydrogenchloride; acetic anhydride In 1,2-dichloro-ethane | 1 Acetylation of dodecylbenzene to form dodecylacetophenone. 900 g of 1,2-dichloroethane and 480 g, corresponding to 3.6 mols, of aluminium chloride are introduced successively, with stirring, into the reactor which has been flushed with nitrogen. 199 g, corresponding to 1.95 mols, of acetic anhydride are then introduced into the resulting suspension, taking care of that the temperature does not exceed approximately 30° C. The medium is stirred at approximately 30° C for some 30 minutes until the aluminium chloride has dissolved completely. 406 g of the concentrated solution of dodecylbenzene in 1,2-dichloroethane obtained in the preceding step, which corresponds to 1.5 mols of dodecylbenzene, are then introduced gradually, keeping the temperature below 30° C. When the introduction of dodecylbenzene is complete, the temperature of the medium is raised to 40° C and is kept at this temperature for 2 hours. At the end of this period of time, evolution of hydrogen chloride, originating from the side reaction between the acetic acid formed and aluminium chloride, has practically ceased. The reaction mixture is then poured slowly into 2 liters of hydrochloric acid (6 to 7 mols/liter) in order to destroy the catalyst. The resulting mixture is heated under reflux for 1 hour. After the upper organic phase has been isolated by decanting, it is evaporated under reduced pressure. The solid collected is slightly brownish. This product consists of the para isomer together with small amounts of impurities. The composition, determined by gas phase chromatographic analyses and by gel permeation, is as follows: The yield of p-dodecylacetophenone is as much as 92%. The crude p-dodecylacetophenone can be used directly, without prior purification, for the synthesis of α-(p-dodecylphenyl)-indole. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With aluminium trichloride; aluminium In ammonia; water; decalin the Fe-complex, alkylbenzene, AlCl3, and Al were stirred (N2) and heated in decaline (180°C,12 h); after hydrolysis (0°C), aq. NH3 (pH=8) was added to remove Al(3+); after filtration, the prod. was pptd. by addn. of an aq. soln. of KPF6;; the ppt. was dissolved in CH2Cl2, dried with MgSO4, concnd., repptd. by addn. of excess dry pentane addn., and recrystd. from hot EtOH; IR and (1)H-NMR spectroscopy;; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Stage #1: 1-dodecylbenzene With sulfuric acid at 90℃; for 1h; Stage #2: With potassium hydroxide In water | 1 A mixture of 1-phenyldodecane (7.5 g, 30.5 mmol) and concentrated H2SO4 (8.4 mL) was stirred vigorously at 90 0C for 1 h, cooled to room temperature, and then gradually poured with stirring into 10% aqueous KOH solution (175 mL). The resulting white precipitate was collected by filtration, washed with cold water (40 mL) and dried to give potassium 4-dodecylbenzene sulfonate (10.6 g, 29.1 mmol, 84%). This salt (10.0 g, 27.5 mmol) and POCI3 (4.2 g, 27.4 mmol) were stirred at room temperature and gradually heated to 170 0C. The hot reaction mixture was poured into cold water and extracted with CHCl2. The organic layer was washed with water, dried over anhydrous Na2SO4, and filtered. Evaporation of the volatiles yielded /?-dodecylbenzenesulfonyl chloride as a pale yellow liquid (9.2 g, 97%) which eventually became crystalline, mp 33 0C; 1H NMR (300 MHz, CDCl3) δ 0.88 (t, 3H, J = 6.5), 1.20-1.38 (m,18H), 1.60-1.68 (m, 2H), 2.72 (t, 2H, J = 7.5 Hz), 7.40 (d, 2H, J = 8.4 Hz), 7.79 (d, 2H, J = 8.4 Hz); 13C NMR (75 MHz, CDCl3) δ 14.1, 22.6, 29.1, 29.3, 29.3, 29.5, 29.6, 30.9, 31.9, 36.0, 127.0, 129.6, 141.7, 151.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: Pyromellitic dianhydride With aluminum (III) chloride In 1,2-dichloro-ethane at 16℃; Stage #2: 1-dodecylbenzene With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 15 - 20℃; for 3.5h; | 3 Preparation of 2,5-Bis(4-dodecylbenzoyl)terephthalic Acid To a mixture of 492 grams of aluminum chloride and 988 mL of 1,2-dichloroethane was added 192 grams of benzene-1,2,4,5-tetracarboxylic acid dianhydride (pyromellitic dianhydride). The resulting mixture was cooled to 16° C. and a solution of 434 grams of 1-dodecylbenzene, 123 grams of diisopropylethylamine and 480 mL of 1,2-dichloroethane was added over a period of 3.5 hours, keeping the temperature between 15° C. and 20° C. during the addition. The mixture was stirred overnight at room temperature and poured into a beaker of 1000 grams of ice and 1000 grams concentrated hydrochloric acid. The mixture was stirred for one hour and the liquid was poured from the coagulate. The mixture was divided into 800 mL portions and each portion was worked up as follows. To 800 mL of the mixture was added 800 mL of tetrahydrofuran, 800 mL of ethyl acetate, and 800 mL of water. The mixture was stirred and phase split. The organic phase was filtered and the filtrate was concentrated in vacuo. The residues were combined. To 127 grams of the combined residue was added 800 mL of ethyl acetate and the mixture was stirred until a suspension of a fine solid resulted. The solid was collected by filtration and washed with 50 mL of ethyl acetate. The solid was dried to give 2,5-bis(4-dodecylbenzoyl)terephthalic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With aluminum (III) chloride In dichloromethane at 10 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With pyridine; aluminum (III) chloride In 1,2-dichloro-ethane at -20 - -15℃; for 0.333333h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; thionyl chloride In dichloromethane | 1.b Example 1 b) The 5-chloro-2-iodo-isophthalic acid (product Example 1a, 3.8 g, 12 mmol) is added to SOCl2 (30 mL, excess) and the mixture is refluxed under nitrogen for 2 days. The excess SOCl2 is evaporated under reduced pressure, then the resultant oil containing the 5-chloro-2-iodo-isophthaloyl dichloride (4.2 g, 12 mmol) is dissolved in dichloromethane (50 mL). To this solution, 1-phenyldodecane (10 g, 47 mmol) and AlCl3 (4.7 g, 35 mmol) are added at 0° C. The mixture is stirred from 0° C. to room temperature overnight. After quenching with 1M HCl solution, the residue is extracted by dichloromethane. The mixture is dried over MgSO4 and purified by column chromatography (silica gel, hexane/ethyl acetate=80:1) to afford the chloro-iododibenzoylbenzene as a colorless oil. Yield 2.3 g (27%). FD-MS (8 kV): m/z=727.7. 1H NMR (250 MHz, CDCl3-d) δ ppm 0.88-0.90 (m, 6H, CH3), 1.26-1.30 (m, 32H, CH2), 2.69 (t, J=7.3, 4 H, CH2), 7.27-7.41 (m, 6H, Ar), 7.75 (t, J=7.9, 4 H, Ar); 13C NMR (62.5 MHz, CD2Cl2-d2): 13C NMR (250 MHz, CD2Cl2-d2): δ ppm 14.3, 23.1, 29.7, 29.8, 29.9, 30.0, 31.4, 32.3, 36.5, 128.8, 129.4, 130.9, 132.9, 135.3, 148.2, 151.1, 195.4. |
Yield | Reaction Conditions | Operation in experiment |
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91% | With aluminum (III) chloride In 1,2-dichloro-ethane at 0 - 20℃; for 4h; | 0287] 2-bromo-1-(4-dodecylphenyl)ethanone (18a): [0287] 2-bromo-1-(4-dodecylphenyl)ethanone (18a): To a solution of AId3 (3.13 g, 23.5 mmol) in dichloroethane (2.0 M) was added bromoacetyl bromide (2.13 mL, 24.5 mmol) and phenyldodecane (5.89 g, 20.4 mmol) sequentially at 0 °C. The mixture was warmed slowly to r.t. over 4 hours. The reaction was then cooled to 0°C and the additional aluminum chloride was quenched with water. The solution was extracted three times into EtOAc, dried over MgSO4, and evaporated. The crude material was purified via flash chromatography to yield the title product as yellow oil (91% yield). Rf= 0.55 (10% EtOAc in hexanes). 1H NMR (300 MHz, CDCI3) 6 7.89 (d, J = 8.1, 2H), 7.28 (d, J = 8.1, 2H), 4.42 (s, 2H), 2.66 (t, J = 7.7, 2H), 1.63 (m, 2H), 1.28 (m, 18H), 0.88 (t, J = 6.5, 3H). 13C NMR (75 MHz, CDCI3) 6 190.69,149.76, 131.49, 128.94, 128.75, 35.97, 31.83, 30.97, 29.56, 29.47, 29.36, 29.28, 29.18, 22.61, 14.05. |
Yield | Reaction Conditions | Operation in experiment |
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71.7% | With potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene; toluene | S.1 Synthesis Example 1, Synthesis Example 1, Synthesis of Compound-1 A mixture of bis(biphenyl-4-yl)amine 10.0g(31.1mmol), 4,4'-Diiodobiphenyl 5.28g (30.0mmol), anhydrous potassium carbonate 5.39g(39.0mmol), copper powder 0.083g (1.3mmol), dodecylbenzene 12ml and xylene 24ml was stirred and heated. After xylene was evaporated the mixture was reacted at 210 - 215°C for 4 hours. Furthermore copper powder 0.083g(1.3mmol) was added to the mixture, additional reaction was proceeded for 4.5 hours. After cooling to 90°C, toluene was added to the reaction mixture, and the reaction mixture was cooled to room temperature. The reaction mixture was filtered and washed with water, methanol and toluene. The residue was extracted with hot toluene and toluene solution was concentrated to dry-up in vacuo. The crude product obtained was purified by recrystallization. 7.38g (yield:71.7%) of N,N,N',N'- Tetrakis (biphenyl-4-yl)-4,4'-diaminobiphenyl was obtained. The melting point was 265°C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 325℃; Autoclave; | General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 245℃; Autoclave; | General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 275℃; Autoclave; | General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 325℃; Autoclave; | General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 325℃; Autoclave; | General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 325℃; Autoclave; | General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 200℃; Autoclave; | General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 200℃; Autoclave; | General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen; at 325℃; under 15001.5 Torr;Autoclave; | General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen; at 275℃; under 15001.5 Torr;Autoclave; | General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 325℃; Autoclave; | General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen; at 245℃; under 15001.5 Torr;Autoclave; | General procedure: Oleic acid (90%, Alfa-Aesar) was used as the unsaturated fattyacid. Pt/SAPO-11 was pre-activated in the oven for 3 h at 150C.The decarboxylation reactions were conducted in a 250 ml stainlesssteel, high pressure autoclave batch reactor (Parr model 4576A).Oleic acid and Pt/SAPO-11 were loaded into the reactor with a massratio of 18:1. Before the reaction started, the air in the reactor wasremoved by flushing with CO2or H2. The pressure was increased tothe desired reaction pressure (usually 20 bar). Under constant stir-ring conditions, the reactor was heated at a rate of 10C/min to thereaction temperature (200-325C) and this temperature was keptconstant during the reaction. Reaction of oleic acid with Pt-aluminawas carried out in a similar manner. After the reaction, the catalystparticles were separated, by filtration, from the liquid product andwashed with acetone for further characterizatio |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84 mg | With [((Me)NN2)NiCl]; isopropyl alcohol; sodium iodide; sodium hydroxide In 1,4-dioxane at 80℃; for 24h; Inert atmosphere; | Alkyl-Alkyl Coupling Reactions; General Procedure General procedure: To a solution of NaOH (32 mg, 0.8 mmol, 1.6 equiv), catalyst 1 (8.4mg, 0.025 mmol, 5 mol%), NaI (37 mg, 0.25 mmol, 0.5 equiv), and i-PrOH (76 μL, 1 mmol, 2 equiv) in dry 1,4-dioxane (2.4 mL), were added alkyl halide (0.5 mmol) and the alkyl-(9-BBN) (1.6 mL, 0.8mmol, 1.6 equiv) under a N2 atmosphere. The mixture was stirred at 80 °C for 24 h. The solution was diluted in Et2O (10 mL), filtered on a short pad of silica, washed with Et2O (3 × 10 mL), and concentrated to dryness under reduced pressure. The residue was purified with a flash purification system to give the coupling product (Tables 1 and 2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46.13% | With Cu3P catalyst supported on SiO2 In dodecane at 340℃; for 6h; Inert atmosphere; | 2.3. Catalytic deoxygenation of oleic acid Oleic acid was used as a model compound for deoxygenation (DO)reaction. The reaction was carried out in a Parr batch reactor. Approximately1 g of supported metal phosphide catalyst and 60 mL of a 5 wt%solution of oleic acid in dodecane were loaded into the reactor. Prior tothe reaction, the reactor was purged with N2, then heated to 340 °C andheld at this temperature for 6 h. The liquid products were analyzed by agas chromatograph equipped with a mass spectrometer (GC-MS). TheDB-1HT was used as a capillary column. In addition, the gas-phaseproducts were not further analyzed because methanation and watergas shift reaction were involved as the main gas phase reaction. Theconversion of oleic acid was calculated according to the followingequations. |
With hydrogen at 325℃; for 2h; | 1 Product analysis 2g of Pt-SAPO 1 1 , prepared as described in Example 1 , were reacted, for 2 hr, with 40 g of oleic acid at 325 C, 20 bar H2 pressure for 2 hr. The conversion of oleic acid was 90% and the liquid hydrocarbon layer contained 60% (wt) of dodecyl benzene. The other constituents of the liquid were branched hydrocarbons and alkyl eyclohexanes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With peracetic acid; iron(II) phthalocyanine; iron(II) benzoylacetonate In water; benzonitrile at 80℃; for 12h; | 23 25 mL reaction flask was successively added with benzoylacetonate (0.025 mmOl), ferrous phthalocyanine(0.0025 mmol) of poly (methylene)(0.75 mmol), peroxyacetic acid (0.75 mmol), lw (0.25 mmol), benzene(lmL), water (lmL) and the reaction mixture was reacted at 80 ° C for 12 h. The reaction was terminated by the addition of aqueous ammonia (2 mL) to remove polymethylhydrogensiloxaneAnd 10 mL of saturated brine was added and extracted with ether (10 mL X3). The organic phases were combined and the solvent was evaporated under reduced pressure. Column chromatographyFrom the yield 65% |
21% | With tert.-butylhydroperoxide; manganese(IV) oxide In dichloromethane; water at -20℃; for 22h; Reflux; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Stage #1: bromoundecane With magnesium In tetrahydrofuran Stage #2: benzaldehyde at 0 - 20℃; Inert atmosphere; Stage #3: With hydrogenchloride; palladium 10% on activated carbon; hydrogen In diethyl ether; water |
Yield | Reaction Conditions | Operation in experiment |
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38.5% | Synthesis of 3,6-Diphenyl-9-tosyl-9H-carbazole 3-Bromo-9-tosyl-9H-carbazole (4.20 g, 13.2 mmol), <strong>[56525-79-2]3,6-diphenyl-9H-carbazole</strong> (4.87 g, 12.5 mmol) and copper(I) oxide (4.54 g, 31.8 mmol) were added to dodecylbenzene (12.3 mL), and the mixture was heated to 220°C under a nitrogen gas environment for 20 hours. After completing the reaction, copper (I) oxide was removed by filtration, and then the filtrate was purified by silica gel column chromatography (developing solvent: hexane/dichloromethane = 50/50) (yield amount: 3.24 g (5.07 mmol), yield: 38.5percent). 1H-NMR (500 MHz, CDCl3) : delta (ppm) 8.58 (d, J = 8.5 Hz, 1H), 8.43 (d, J = 1.5 Hz, 2H), 8.41 (d, J = 8.5 Hz, 1H), 8.14 (d, J = 2.0 Hz, 1H), 7.92 (d, J = 7.5 Hz, 1H), 7.84 (d, J = 8.5 Hz, 2H), 7.75-7.72 (m, 6H), 7.68 (dd, J = 1.5 Hz, J=2.0Hz, 2H), 7.59-7.56 (m, 1H), 7.52-7.45 (m, 5H), 7.42-7.39 (m, 1H), 7.37-7.35 (m, 2H), 2.34 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With copper(l) iodide In 2-methyltetrahydrofuran; toluene at 80℃; for 18h; Inert atmosphere; Schlenk technique; Sealed tube; | Copper-catalyzed cross-coupling non-activated alkyl chloride with phenylmagnesium bromide: general procedure General procedure: To an oven-dried Schlenk tube were added CuI (0.1 mmol, 10 mol%), then the tube was evacuated and backfilled with argon for three times. To this Schlenk tube were added alkyl chloride (1.0 mmol), toluene (2.0 mL) and phenylmagnesium bromide (0.8 mL of a 2.9 mol/L 2-MeTHF solution, 2.3 mmol). The tube was sealed and the mixture was allowed to stir at 80 °C for 18 h. After being cooled to room temperature, the reaction mixture was quenched with HCl aq. (1 N). The aqueous layer was extracted with Et2O three times. The combined organic layer was dried over anhydrous MgSO4, filtered, and evaporated. The residue was purified by column chromatography using petroleum ether (30 - 60oC) as eluent to afford the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 75 %Chromat. 2: 24 %Chromat. | With copper(l) iodide In 2-methyltetrahydrofuran; toluene at 80℃; for 18h; Inert atmosphere; Schlenk technique; Sealed tube; | Copper-catalyzed cross-coupling non-activated alkyl chloride with phenylmagnesium bromide: general procedure General procedure: To an oven-dried Schlenk tube were added CuI (0.1 mmol, 10 mol%), then the tube was evacuated and backfilled with argon for three times. To this Schlenk tube were added alkyl chloride (1.0 mmol), toluene (2.0 mL) and phenylmagnesium bromide (0.8 mL of a 2.9 mol/L 2-MeTHF solution, 2.3 mmol). The tube was sealed and the mixture was allowed to stir at 80 °C for 18 h. After being cooled to room temperature, the reaction mixture was quenched with HCl aq. (1 N). The aqueous layer was extracted with Et2O three times. The combined organic layer was dried over anhydrous MgSO4, filtered, and evaporated. The residue was purified by column chromatography using petroleum ether (30 - 60oC) as eluent to afford the product. |
Yield | Reaction Conditions | Operation in experiment |
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1: 43 %Chromat. 2: 54 %Chromat. | With copper(l) iodide In 2-methyltetrahydrofuran; toluene at 80℃; for 18h; Inert atmosphere; Schlenk technique; Sealed tube; | Copper-catalyzed cross-coupling non-activated alkyl chloride with phenylmagnesium bromide: general procedure General procedure: To an oven-dried Schlenk tube were added CuI (0.1 mmol, 10 mol%), then the tube was evacuated and backfilled with argon for three times. To this Schlenk tube were added alkyl chloride (1.0 mmol), toluene (2.0 mL) and phenylmagnesium bromide (0.8 mL of a 2.9 mol/L 2-MeTHF solution, 2.3 mmol). The tube was sealed and the mixture was allowed to stir at 80 °C for 18 h. After being cooled to room temperature, the reaction mixture was quenched with HCl aq. (1 N). The aqueous layer was extracted with Et2O three times. The combined organic layer was dried over anhydrous MgSO4, filtered, and evaporated. The residue was purified by column chromatography using petroleum ether (30 - 60oC) as eluent to afford the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With C18H24ClN3Ni; sodium iodide; sodium hydroxide In 1,4-dioxane; isopropyl alcohol at 20℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 78.1% 2: 85.6% | Stage #1: triphenylphosphine With lithium In 1,4-dioxane at 20℃; for 3h; Inert atmosphere; Stage #2: 1-dodecylbromide In 1,4-dioxane at 10 - 80℃; for 6.25h; | 6 1) Under the protection of nitrogen, triphenylphosphine was added to the reaction flask equipped with dioxane, and the metal lithium was added under stirring, the molar ratio of metal lithium to triphenylphosphine was 2.4: 1, The reaction was carried out for 3 hours to ensure that the reaction of the triphenylphosphine was complete and the unreacted metal lithium was removed and removed to obtain phenyl phosphine lithium dioxane solution.2) The resulting phenylphosphine lithium dioxane solution of step 1) was cooled to 10 ° C,The system was added to the system by adding brominated n-dodecane, dripping in 15min, incubating for 3 hours, then heating the system to 80 . After incubating for 3 hours, the system was reduced to room temperature, Layer, dry; distillation of dioxane, and then vacuum distillation, were positive dodecyldiphenyl phosphine and n-dodecyl benzene.The yield of the n-dodecyl diphenylphosphine was 78.1% and the yield of n-dodecylbenzene was 85.6% in the same manner as in Example 1, except that the alkyl diphenylphosphine was used to produce alkylbenzene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1-hexene; 1,6-diphenyl-hexa-1,3,5-triene With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In toluene at 100℃; for 2h; Schlenk technique; Inert atmosphere; Stage #2: With palladium on activated charcoal; hydrogen In ethanol; toluene at 20℃; Schlenk technique; | Cross metathesis of 1,6-diphenyl 1,3,5-hexatriene (1) and 1-hexene A Schlenk tube was charged with1 (0.0927 g, 0.40mmol), 1-hexene (0.300 mL, 2,40mmol),toluene (2.0 mL), and fitted with a condenser. A solution of HG2 (0.0106 g, 0.0169mmol, 0.05eq) intoluene (1.0 mL) was added. The mixture was heated (100°C) for 2 hours, cooled down to room temperature, Pd/C (0.010 g) and ethanol (2 mL) was added. Then a balloon filled with hydrogen was connected to the Schlenk tube. The mixture was stirred overnight at room temperature. Then the suspension was filtered and the obtained solution was analyzed by GC-MS (Figure S9, Table S4). |
Yield | Reaction Conditions | Operation in experiment |
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99% | With aluminum (III) chloride In dichloromethane at -10℃; |
Yield | Reaction Conditions | Operation in experiment |
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With 1-butyl-iso-quinolinium hydrogen sulfate; iron(III) chloride at 60℃; for 0.833333h; Autoclave; Inert atmosphere; | 2; 12-15 Example 12 General procedure: Catalyst a is used as a catalyst, catalyst a: ionic liquid S1, and the auxiliary agent is zinc chloride.80 g of benzene and 100 g of 1-chlorododecane were added to the reaction vessel, followed by the addition of 18 g of N-(3-sulfonate)propyl-5-sulfonate isoquinoline trifluoromethanesulfonate ionic liquid. 4.5 g of zinc chloride was added. The air in the autoclave was replaced with nitrogen, pressurized to 0.3 MPa, and heated to 30 ° C for 30 min. The amount of the catalyst and the reaction conditions are shown in Table 3. After the end of the reaction, the supernatant liquid was taken for GC-MS analysis, and the results are shown in Table 4. The lower layer was the catalyst phase, and was re-added to the reaction vessel. The above operation was repeated, and the effect of the catalyst was repeated 10 times without significant change. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63 mg | With C60H72Br2N4Ni; tetrabutylammonium p-toluenesulfonate In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Irradiation; Sealed tube; | 11. Ni-catalyzed C(sp3)-C(sp3) cross-coupling (Figure 2A) General procedure: General Procedure GIn an argon-filled glovebox, a flame-dried 10 mL sealing tube equipped with a Teflon septumand magnetic stir bar was charged with ZrCp2HCl (258 mg, 1.0 mmol, 2.0 equiv.), the reactionvial was sealed tightly and removed from the glovebox, anhydrous THF (1.25 mL), alkene (1.1mmol, 2.2 equiv.) were added by a syringe under an argon atmosphere. The mixture was stirredfor 30 min until a clear yellow solution was obtained.In an argon-filled glovebox, another flame-dried 10 mL sealing tube equipped with a Teflonseptum and magnetic stir bar was charged with alkyl halide (0.5 mmol, 1.0 equiv.), Ni-1 (3.2mg, 0.003 mmol, 0.6 mol%), tetrabutylammonium 4-toluenesulfonate (207 mg, 0.5 mmol, 1.0equiv.), the reaction vial was sealed tightly and removed from the glovebox, the previous clearalkyl zirconium reagent was transferred via syringe over 1 min to this reaction vial under anargon atmosphere. The reaction mixture was then stirred and irradiated with blue LEDs with afan placed above for cooling. After 24 h, the reaction mixture was diluted with CH2Cl2, filteredthrough a short pat of silica gel, and concentrated in vacuum. Purification of the crude productby flash chromatography on silica gel afforded the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: n-Dodec-4-en With Schwartz's reagent In tetrahydrofuran at 50℃; for 5h; Inert atmosphere; Sealed tube; Stage #2: iodobenzene With 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide; triphenylphosphine In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Irradiation; Sealed tube; | 14. Chain walking and cross-coupling General procedure: General procedure JIn an argon-filled glovebox, a flame-dried 10 mL sealing tube equipped with a Teflon septumand magnetic stir bar was charged with ZrCp2HCl (258 mg, 1.0 mmol, 2.0 equiv.), the reactionvial was sealed tightly and removed from the glovebox, anhydrous THF and alkene (1.1 mmol,2.2 equiv.) were added by a syringe under an argon atmosphere. The mixture was stirred at 50oC for a specific time until a clear yellow solution was obtained.In an argon-filled glovebox, another flame-dried 10 mL sealing tube equipped with a Teflonseptum and magnetic stir bar was charged with corresponding organic halide (0.5 mmol, 1.0equiv.), Ni cat. (1 mol%), tetrabutylammonium 4-toluenesulfonate (207 mg, 0.5 mmol, 1.0equiv.), the reaction vial was sealed tightly and removed from the glovebox, the previous clearalkyl zirconium reagent was transferred via syringe over 1 min to this reaction vial under anargon atmosphere. The reaction mixture was then stirred and irradiated with blue LEDs with afan placed above for cooling. After 24 h, the reaction mixture was diluted with CH2Cl2, filteredthrough a short pat of silica gel, and concentrated in vacuum. Purification of the crude productby flash chromatography on silica gel afforded the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 85% 2: 6% | With nickel(II) bromide dimethoxyethane; 5,5'-bis(tris(3,5-diisopropylphenyl)methyl)-2,2'-bipyridine; zinc In N,N-dimethyl acetamide at 60℃; for 14h; Inert atmosphere; Glovebox; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 32.84% 2: 8.31% 3: 5.01% | With Cu3P catalyst supported on ultra-stable zeolite Y In dodecane at 340℃; for 6h; Inert atmosphere; | 2.3. Catalytic deoxygenation of oleic acid Oleic acid was used as a model compound for deoxygenation (DO)reaction. The reaction was carried out in a Parr batch reactor. Approximately1 g of supported metal phosphide catalyst and 60 mL of a 5 wt%solution of oleic acid in dodecane were loaded into the reactor. Prior tothe reaction, the reactor was purged with N2, then heated to 340 °C andheld at this temperature for 6 h. The liquid products were analyzed by agas chromatograph equipped with a mass spectrometer (GC-MS). TheDB-1HT was used as a capillary column. In addition, the gas-phaseproducts were not further analyzed because methanation and watergas shift reaction were involved as the main gas phase reaction. Theconversion of oleic acid was calculated according to the followingequations. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Stage #1: 1-dodecene With tetrabutylammonium borohydride; ethyl iodide In tetrahydrofuran at 25℃; for 20h; Stage #2: iodobenzene With bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide In water at 80℃; for 16h; Inert atmosphere; | Typical procedure for Suzuki-Miyaura coupling of organoborane generated by the PV method General procedure: Ethyl iodide (172 mg, 1.1 mmol) and magnetic stirring bar were placed at the bottom of a test tube (15mm f × 130 mm), to which Galden HT-135 (1.5 mL) and Galden HT-200 (0.5 mL) were added slowly using a syringe in order. Subsequently, nBu4NBH4 (300 mg, 1.1 mmol), a solution of 4-methylstyrene(1a, 120 mg, 1.0 mmol) in THF (2.5 mL) were added slowly in order, forming three layers. A rubber septum was fitted to the test tube, and a needle equipped with a balloon, which acted as a reservoir of borane gas during the reaction, was then pricked into the septum. The air in the test tube was removed by a syringe until the balloon was completely flattened. The test tube was stirred slowly for 2 h at 25 °C, taking care not to mix the layers. After 2 h, iodobenzene (214 mg, 1.05 mmol), an aqueous NaOH solution (2.5 M, 1.0 mL), and PdCl2(PPh3)2 (28 mg, 4 mol%) were added under argon atmosphere. Asmall condenser (cold finger type) was fitted to the test tube and the reaction mixture was heated at80 °C for 16 h. The organic layer was taken up with a glass pipette to a separating funnel, and washed with water and brine three times. The organic layer was dried over Na2SO4. After filtration, the solvent was evaporated. The residue was then purified by column chromatography on silica gel, eluting hexane afforded 2-(p-tolyl)ethylbenzene (6a, 142 mg, 72%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With aluminum (III) chloride In dichloromethane at 20℃; | 1 Synthesis of p, p'-zidodecylbenzophenone (C12-BP-C12) (1) Anhydrous aluminum chloride (1.35 g, 10.14 mmol),Dodecylbenzene (2 g, 8.12 mmol) and oxalyl chloride in 2 mL dichloromethane with stirring at room temperatureIt was added slowly to the mixture (0.52 g, 4.06 mmol).After leaving overnight, the dichloromethane is evaporated andThe residue was decomposed with ice-cold water and extracted with ether.The extracted ether was washed with distilled water and a 10% K2CO3 solution and dried over Na2CO3.The Et2O residue was separated by chromatography (hexane containing silica gel / 4% tetrahydrofuran) and further separated by preparative GPC (eluent: chloroform).After concentration, C12-BP-C12 (1) becomes a yellow oilObtained (1.0 g, 47%).The product was confirmed by MALDI-TOF MS and 1H NMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With sulfuric acid; acetic acid | A Bis(4-n-dodecylphenyl)iodonium tetrakis(pentafluorophenyl)borate (PAG2) Example A Bis(4-n-dodecylphenyl)iodonium tetrakis(pentafluorophenyl)borate (PAG2) In a suitable reaction vessel equipped with a magnetic stirrer was placed a mixture of 1-phenyldodecane (34.5 g, 140 mmol), potassium periodate (15 g, 70 mmol), acetic anhydride (30 g, 294 mmol) and acetic acid (10 g). The reaction mixture was cooled with an ice bath. To this solution carefully was added dropwise a solution of sulfuric acid (16 g) dissolved in acetic anhydride (20 g). After the addition, reaction mixture was stirred overnight. Then, water (20 ml) was added followed by an aqueous solution of NaCl (10.2 g, 170 mmol dissolved in 50 ml of water). The reaction mixture was cooled to 0° C. and the resulting precipitate was collected. The precipitate was then washed with cold isopropanol and methanol and air dried overnight to obtain di(p-dodecylphenyl)iodonium chloride (13 g, 31% yield). |
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H412 | Harmful to aquatic life with long-lasting effects |
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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