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CAS No. : | 106-32-1 | MDL No. : | MFCD00009552 |
Formula : | C10H20O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YYZUSRORWSJGET-UHFFFAOYSA-N |
M.W : | 172.26 | Pubchem ID : | 7799 |
Synonyms : |
Octanoic acid ethyl ester
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.9 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 51.47 |
TPSA : | 26.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.84 cm/s |
Log Po/w (iLOGP) : | 2.78 |
Log Po/w (XLOGP3) : | 3.54 |
Log Po/w (WLOGP) : | 2.91 |
Log Po/w (MLOGP) : | 2.58 |
Log Po/w (SILICOS-IT) : | 2.78 |
Consensus Log Po/w : | 2.92 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.61 |
Solubility : | 0.423 mg/ml ; 0.00245 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.78 |
Solubility : | 0.0288 mg/ml ; 0.000167 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.17 |
Solubility : | 0.116 mg/ml ; 0.000673 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 1.93 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P210-P264-P280-P302+P352+P332+P313+P362+P364-P370+P378-P403+P235-P501 | UN#: | N/A |
Hazard Statements: | H227-H315 | 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 |
---|---|---|
91.1% | With hydroxylamine hydrochloride; potassium hydroxide In ethanol; water at 5 - 55℃; for 3 h; | To the 1000 mL four-necked flask was added hydroxylamine hydrochloride(48.7 g, 0.70 mol, 1.4 eq), water (50 g),Ethanol (200 g, 2.3X), stirred at room temperature until hydroxylamine hydrochloride was dissolved,Then joinEthyl octanoate(86.7 g, 0.5 mol, 1.0 eq), Stirred at room temperature to form a two-phase system, and then cooled to 5 ~ 10 ,Slowly add 40percent KOH (168 g, 1.2 mol, 2.4 eq), Dripping finished, and then heated to 50 ~ 55 , insulation reaction 3 h,GC in the control of n-octanoic acid ethyl ester raw materials disappeared, stop the reaction,Cooled to 5-10 ° C, concentrated hydrochloric acid (90 mL) was added slowly,Adjust the pH = 6.4 ~ 6.7, precipitate a large number of white solid, filter,Dried at 50 for 8 h, the crude product was recrystallized from benzene,A white flocculent solid was 78.8 g, yield 91.1percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With C30H34Cl2N2P2Ru; potassium methanolate; hydrogen; In tetrahydrofuran; at 100℃; under 38002.6 - 76005.1 Torr; for 15h;Glovebox; Autoclave; | General procedure: In a glove box, add a ruthenium complex Ia (0.3 to 0.7 mg, 0.0002 to 0.001 mmol) to a 300 mL autoclave,Potassium methoxide (35-700 mg, 0.5-10 mmol), tetrahydrofuran (4-60 mL), and ester compounds (10-200 mmol).After sealing the autoclave, take it out of the glove box and fill it with 50 100atm of hydrogen.The reaction kettle was heated and stirred in an oil bath at 100 C for 10 to 336 hours.After the reaction kettle was cooled in an ice-water bath for 1.5 hours, the excess hydrogen was slowly released.The solvent was removed from the reaction solution under reduced pressure, and the residue was purified with a short silica gel column to obtain an alcohol compound. The results are shown in Table 5. |
80% | With methanol; sodium tetrahydroborate; sodium ethanolate; at 40℃; | <strong>[106-32-1]Ethyl octanoate</strong> (105 g, 0.61 mol) was dissolved in methanol (420 mL, 4 V) and stirred, then pumped into the coil with pump A at a rate of 5.6 g/min, sodium borohydride (33.86 g, 0.92 mol), EtONa (1.24g, 0.018mol) was dissolved in methanol (105mL, 1V) and pumped to a 240mL coil with pump B at a rate of 1.5g / min. The coil was immersed in a 40 C oil bath, and the outlet was sampled by HPLC. The system was subjected to quenching extraction in a 2 L four-necked flask and subjected to column chromatography to obtain 70 g of a product in a yield of 80%. |
With [RuCl2((E)-N-(2-(diphenylphosphino)benzyl)-1-(6-((diphenylphosphino)methyl)pyridin-2-yl)methanimine)]; hydrogen; sodium ethanolate; at 80℃; under 37503.8 Torr; for 0.66h;Autoclave;Catalytic behavior; | General procedure: Ester, ruthenium catalyst , metal alkoxide co-catalyst (used as a solid or some alcoholic solution) and optionally solvent (see Table 1) were loaded altogether in an 100 mL or 1L autoclave equipped with a mechanical stirring device, pressure and internal temperature sensors and a heating/cooling system for internal temperature regulation. Sealed autoclave was then purged under stirring with nitrogen (3 times 5 bars) and hydrogen (3 times 5 bars) before being pressurized to required hydrogen pressure via an hydrogen tank equipped with a way out pressure regulator and also an internal pressure sensor to follow and determine hydrogen consumption. Reaction mixture was then heated to required temperature and hydrogen pressure into the autoclave was maintained to the desired value during the whole reaction. Upon reaction completion also determined by GC analysis with complete disappearance of both starting material and mixed ester coming from transesterification reaction with product and eventually with metal alkoxide co-catalyst and/or alcoholic solvent, autoclave was then cooled down to 25 C. It was then depressurized and purged with nitrogen (3 times 5 bars) and reaction mixture was then transferred to a round-bottomed flask and lights compounds were removed under vacuum. Crude product was then flash distilled in order to determine the quantity of residues formed during the reaction and yield was calculated based on GC purity of distilled product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.1% | With hydroxylamine hydrochloride; potassium hydroxide; In ethanol; water; at 5 - 55℃; for 3h; | To the 1000 mL four-necked flask was added hydroxylamine hydrochloride(48.7 g, 0.70 mol, 1.4 eq), water (50 g),Ethanol (200 g, 2.3X), stirred at room temperature until hydroxylamine hydrochloride was dissolved,Then joinEthyl octanoate(86.7 g, 0.5 mol, 1.0 eq), Stirred at room temperature to form a two-phase system, and then cooled to 5 ~ 10 ,Slowly add 40% KOH (168 g, 1.2 mol, 2.4 eq), Dripping finished, and then heated to 50 ~ 55 , insulation reaction 3 h,GC in the control of n-octanoic acid ethyl ester raw materials disappeared, stop the reaction,Cooled to 5-10 C, concentrated hydrochloric acid (90 mL) was added slowly,Adjust the pH = 6.4 ~ 6.7, precipitate a large number of white solid, filter,Dried at 50 for 8 h, the crude product was recrystallized from benzene,A white flocculent solid was 78.8 g, yield 91.1% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diethyl ether; 2-pentylmagnesium chloride zuletzt auf dem Wasserbad; | ||
With diethyl ether; s-butylmagnesium chloride zuletzt auf dem Wasserbad; | ||
With (1,1-dimethyl-propyl)-lithium In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrazine hydrate; In ethanol; | Example N n-octanoic acid hydrazide Following the method of Example M, ethyl octanoate (17.2 g, 0.10 mole) and hydrazine monohydrate (7.35 ml, 0.15 mole) in ethanol (75 ml) gave the product by triturating the residual oil with ether to give a solid with melting point 85-87C (5.50 g, 35%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With Mo(Oxo)/C; at 90℃; for 2h;Catalytic behavior; | [0060] Interestingly, aldehydes were also found to undergo oxidative esterification under the reaction conditions utilized. Both octanal and benzaldehyde were independently subjected to the reaction conditions for transesterification (Table 7, entries 1 and 2). Both aldehyde substrates were converted to the corresponding ethyl ester by the supported Mo catalyst. Aromatic cinnamaldehyde and para-tolualdehyde were also subjected to the reaction conditions, however, the enthalpy of desorption from the carbon surface was greater than that of acyl cleavage and either no yield was observed for these 2 substrates respectively (Table 7, entries 3 and 4) |
30% | With manganese(IV) oxide; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-butyl-3-methylimidazolium Tetrafluoroborate; at 20℃; for 24h;Inert atmosphere; | General procedure: In a typical procedure, a capped vessel was charged with ionic liquid BmimBF4 (0.5 mL) and put under positive pressure of nitrogen. DBU (0.5 mmol) and Cs2CO3 (1.5 mmol) were added followed by the aldehyde (0.5 mmol) and MnO2 (1.5 mmol). The reaction mixture was stirred for a few minutes and alcohol (1.5 mmol) was added. The reaction mixture was stirred at ambient temperature for 24 h. The mixture was then filtered through a thin pad of silica, which was washed with ethyl acetate (30 mL). The filtrate was analyzed by TLC and 1H NMR and then concentrated under vacuum. The resulting residue was purified by flash chromatography on silica gel where needed. |
74%Chromat. | With oxygen; at 100℃; under 3750.38 Torr; for 5h;Autoclave; | General procedure: Octanal (128 mg, 1.00 mmol), ethanol (2 mL, 34.3 mmol), 1 wt% gold catalyst (100 mg, Au 0.5 mol%), tridecane as an internal standard, and a magnetic stirring bar was charged in an autoclave. Oxygen gas was filled in the autoclave with 0.5 MPa (the gauge pressure). The reaction was carried out at 100 C. After 5 h, the reaction mixture was extracted with ethanol and filtered. The filtrate was analyzed by gas chromatography using an Agilent7890A or a Shimadzu GC2014 with an HP-5 column. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In diethyl ether at 70℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 60℃; Yield given. Yields of byproduct given; | ||
at 60℃; for 0.5h; Yield given. Yields of byproduct given; | ||
at 60℃; for 0.5h; Yield given. Yields of byproduct given; |
With C118H83N4ORh Inert atmosphere; regioselective reaction; | ||
With C28H6Ag2Au2F24N2 In cyclohexane for 12h; Inert atmosphere; regioselective reaction; | ||
With [N-(2-ethoxy-2-oxoethyl)-N'-(mesityl)imidazolin-2-ylidene]gold chloride In dichloromethane for 24h; Inert atmosphere; | ||
With C36H7AgBF39N6O at 20℃; for 9h; Inert atmosphere; Schlenk technique; regioselective reaction; | ||
With carbon dioxide; (,5-bis(trifluoromethyl)-4-bromo]pyrazol-1-yl}borate)Cu(NCMe) at 40℃; for 8h; Schlenk technique; Supercritical conditions; regioselective reaction; | ||
Stage #1: hexane With C39H35BrCuNO; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate for 0.25h; Schlenk technique; Inert atmosphere; Stage #2: diazoacetic acid ethyl ester for 21h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Lipase enzyme preparation In benzene Ambient temperature; Lipases catalyzed transesterification; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.7% | With sulfuric acid; for 5h;Reflux; | Mix 14.421 g (0.1 mol, 1.0 eq) of Compound 1 and 5.889 g (0.13 mol, 1.3 eq) of ethanol, add 1 mL of sulfuric acid, heat under reflux for 5 hours, neutralize with sodium hydroxide solution, and distill under reduced pressure to obtain 16.395 g Colorless liquid product. Based on compound 2, the colorless liquid product has a purity of 99.5% and a yield of 94.7%. |
90.6% | With 8-hydroxyquinoline sulphate; at 85℃; for 4h; | In a 100 mL three-necked flask, 0.08 mol of n-octanoic acid, 0.40 mol of ethanol and 0.04 mol of 8-hydroxyquinolineHydrogen sulfate ion liquid, control the reaction temperature of about 85 , equipped with reflux condenser, stirring at constant temperature 4h. The reaction is stopped, the unreacted ethanol is removed under reduced pressure, the mixture is transferred to a separatory funnel, and the appropriate amount of saturated brine is added. After shaking, the layers are discarded and the lower layer of water is discarded. After the last, the resulting oil is the productOctanoate, yieldFor 90.6%. |
99%Chromat. | With sulfuric acid; for 4h;Reflux; | General procedure: General procedure for the synthesis of compounds (6a-p); organic acid (0.40 mmol.), and catalyst (0.0005 mmol.) was combined with 20 mL ethanol in a 50 mL round bottomed flask equipped with a stir bar. Reaction was allowed to stir at reflux temperature for the appropriate amount of time (4 h). After completion of reaction, the reaction mixture was concentrated in vacuum to give a crude product which was analyzed by 1H NMR and GC-MS. |
With acidic cation exchange resin Amberlyst 70; In water; at 50 - 145℃;Flow reactor; Green chemistry; | General procedure: Acetic acid and ethanol at a weight ratio of 1:2 or 1:3 were mixed at 30 C., and then introduced into the lower part of the vertical reactor at a liquid hourly space velocity (LHSV) of 3 hour-1. The reaction was performed at 115 C. The esterized mixture was output from the upper part of the vertical reactor, and collected to be analyzed by gas photography. The acid value of the product was determined by titration, and the conversion rate and the selectivity were analyzed. The results were shown in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diethyl ether at 5℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Lipase enzyme preparation In benzene Ambient temperature; Lipases catalyzed transesterification; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With bromobenzene; hydrogen; at 40℃; under 1500.15 Torr; for 3h;Autoclave; | General procedure: In a typical run, a 50 mL stainless steel autoclave equipped with a transducer for online pressure monitoring was charged under air of Pd-pol (10.6 mg, Pd: 0.5 mol%), the substrate (carboxylic acid or ester, 1.0 mmol), bromobenzene (0.1 mmol, 15.7 mg) and alcohol (5.0 mL). The autoclave was then purged three times with hydrogen, then pressurized with 2 bars H2, set on a magnetic stirrer and heated to 40 C. After the minimum time needed to reach reaction completion, the autoclave was let to reach room temperature, the hydrogen was vented and the autoclave opened. When necessary, 3.0 mL diethyl ether was added to the mixture at the end of reaction in order to dissolve organic reactants and products. The catalyst was recovered by centrifugation. The yields were assessed by GLC analysis of the organic solution by using biphenyl (50.0 mg) as internal standard. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | for 132h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 88 percent / n-BuLi / tetrahydrofuran; hexane / 12 h / -78 - 20 °C 2: 95 percent / Amberlyst-15 / benzene / 12 h / Heating 3: 83 percent / diethyl ether / 1) -78 deg C, 0.5 h; 2) rt, 48 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chlorosulfonic acid | 108.B Step B. Step B. 4-[(Hexylamino)carbonyl]amino}benzenesulfonyl chloride N-Hexyl-N'-phenylurea (6.0 g, 27.23 mmol) was added with stirring over 20 minutes to chlorosulfonic acid (17 mL) at 0° C. The reaction was heated at 60° C. for 2 hours. The mixture was cooled and poured cautiously into ice with stirring. The aqueous phase was extracted with ethyl acetate and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent removed in vacuo. The residue was purified by flash chromatography on silica gel Merck-60 (eluant: 3:1 ethyl hexane-acetate) to furnish the title compound (6.2 g, 19.45 mmol). MS ((-)ESI, m/z): 317 [M-H]- |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(Example 3) Synthesis of N-[2-(1-methylpyrrolidin-2-yl)ethyl]caprylamide (Compound 3) toluene (1.0 ml), dried using MS 4A, was mixed with 1.48 ml of a n-hexane solution of 15% Me3Al. With the mixture being cooled in an ice-methanol bath, 0.25 ml (1.16 mmols) of 2-(2-aminoethyl)-1-methylpyrrolidine was added dropwise over about 2 minutes.. After stirring for 20 minutes, the temperature was raised to room temperature, and 0.5 ml of a toluene solution of 0.2 g (1.16 mmols) of caprylic acid ethyl ester was added dropwise over 1 minute.. After stirring for 2 hours at 70C, the mixture was cooled with ice, and 10 ml of 1N NaOH was added dropwise.. The mixture was stirred for 10 minutes, and water and ethyl acetate were added.. Then, the mixture was separated into respective layers, and the organic layer was washed twice with 20 ml of a saturated aqueous solution of sodium chloride.. After this layer was dried over anhydrous magnesium sulfate, it was concentrated under reduced pressure on a 30C water bath to obtain the captioned compound (yield 0.22 g).. This compound was subjected to silica gel column chromatography (mobile phase: CHCl3:MeOH (19:19:1)) for purification. NMR and mass spectrum confirmed the purified compound to have the following structure: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Candida antarctica lipase B In cyclohexane at 20℃; Enzymatic reaction; | ||
With Candida antartica lipase B immobilised on Accurel enzyme carrier beads In decane; cyclohexane at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrazine hydrate; acetic acid; at 100℃; for 12h; | To a stirred solution of the <strong>[106-32-1]octanoic acid ethyl ester</strong> (105 mmol, 39.5 g) in glacial acetic acid(25.5 mL) was added hydrazine hydrate (525 mmol, 25.5 mL), and the reaction was heated at 100C for 12 h. After cooling, the volatiles were removed in vacuo, the residue was dissolved in ethyl acetate (300 mL). The organic layer was washed with water (100 mL), saturated NaHCC>3 (3 x 100 mL), brine (100 mL), dried (IN^SCU), filtered, and concentrated under reduced pressure. The residue was recrystallized from a mixture of ethyl acetate (200 mL) and hexanes (300 mL) to afford 6-butyl-5-(4- cyclohexyloxy-phenyl)-2H-pyridazin-3-one. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20%Spectr. | With 1-hydroxytetraphenyl-cyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-mu-hydrotetracarbonyldiruthenium(II); In Triethylene glycol dimethyl ether; at 110℃; under 11.2511 Torr; for 48h;Enzymatic reaction; | General procedure: General experimental conditions and results on the DKR reactions are collected in Table2. First, 110mg (1mol%) of the Shvo's catalyst, 70ml of the corresponding glyme, racemic 1-(aryl)ethylamine and the corresponding acyl donor were placed in a three-necked 100ml round-bottom flask, equipped with a thermometer, a magnetic stirrer bar, a capillar and a Soxhlet head (50ml) with a reflux condenser. The enzyme (Novozyme 435) was packed in 4 porous polyethylene bags, 50mg in each. In the case of the slower reacting 1-(naphthyl)ethylamine, 6 bags containing 300mg of enzyme in total were utilized. The bags containing the enzyme were placed into an extraction chamber of the Soxhlet extractor together with 5mm glass beads. In this way the ?dead volume? of the Soxhlet extractor was reduced to approximately 20ml. Disposable thermo-sensors were placed between the enzyme bags. If desired, with proper construction of the reflux condenser, a thermometer could also be inserted into the glass beads. The outlet of the reflux condenser was connected to an inlet of a membrane pump equipped with vacuum control unit. The argon inlet was connected to the capillar and to the gas inlet of the pump. We recommend the incorporation of a 1-2l buffer flask between the apparatus and the vacuum pump for controlling the vacuum oscillation. The use of Teflon thermostable grease for the hot joints is likewise recommended. The side arm of the extractor should be thermally insulated. Loops of rubber tubing with cooling water circulation can be applied around the extraction chamber for additional cooling of the enzyme. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With D-(+)-glucose; In aq. buffer; at 15℃; for 16h; | General procedure: Whole-cell biotransformations were performed using both growing and resting cells. For growing cells, 2 ml TB medium in a 15 ml Falcon tube was inoculated with a pre-culture of E. coli BL21-CodonPlus(DE3)-RP cells containing the recombinant plasmid with the BVMO gene. The cells were grown for 3 h at 30 C and with shaking at 150 rpm. Immediately after adding IPTG, the biotransformation reaction was initiated by adding the substrate to a final concentration of 5 mM. To boost the regeneration of NADPH, glucose (25 mM) was also added at the moment of induction. Biotransformations were carried out for 16 h at 15 C and at a shake rate of 150 rpm. The level of conversion was measured by comparing E. coli BL21-CodonPlus(DE3)-RP expressing BVMO3 with cells from the same E. coli strain carrying pET-22b(+) without the BVMO3 gene, that served also as a blank for side reactions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With gold supported on zirconium oxide; oxygen; caesium carbonate; at 30℃; under 760.051 Torr; for 48h; | General procedure: Known amounts of catalyst, base and alcohol (RCH2OH,2 mmol) were mixed with methanol in a round bottomed flask.The reaction device was sealed after having been filled with O2at ambient pressure and then kept at a specified temperature witha magnetic stirrer. During the reaction, the O2 was supplemented;a small amount of the mixture was extracted and filtered toremove the catalysts. The filtrate was analyzed using theGC-2014C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | General procedure: To a solution of 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl iodide (0.22 mL, 1.0 mmol), ethyl benzoate (0.16 mL, 1.1 mmol) in Et2O (3 mL) was added at -80C methyllithium (1.5 M in Et2O with lithium bromide; 0.73 mL, 1.1 mmol) and stirring was continued for 30 min at the same temperature where diethyl-aluminium chloride (1 M in n-hexane; 1.1 mL, 1.1 mmol) was gradually added and further stirring for 15 min at -80 C. In a separate flask, lithium bromide (0.12 g, 1.4 mmol), triethyl phosphonoacetate (0.26 mL, 1.3 mmol), and THF (1 mL) was mixed at 0 C where triethylamine (0.19 mL, 1.4 mmol) was added and the solution was stirred for 10 min at room temperature. This mixture was slowly introduced to an aluminium acetal solution prepared above with the aid of cannula and the whole mixture was further stirred for 1 h at room temperature. To this solution were successively added Et2O (3 mL), NaF (0.185 g, 4.4 mmol) and H2O (59 mg, 3.3 mmol), which was stirred for 0.5 h at room temperature. Filtration with a pad of silica gel and concentration furnished a crude mixture which was purified by silica gel column chromatography (n-hexane:CH2Cl2=6:1) to afford 0.484 g (0.979 mmol, 98% yield, E:Z=>99:1) of the title compound 5ca as a colourless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h;Inert atmosphere; | 10066] Compound lb (391 mg, 1 mmoE) and K2C03 (204 mg, 1.5 mmoE) were dissolved in anhydrous DMF (10 mE),and 8-ethyl caprylate (276 mg, 1.1 mmoE) was slowly drop- wise added into the solution with nitrogen protection, andstirred for 16 hours at room temperature. The resulted system was regulated to pH=7.-S with 1 M hydrochloric acid solution and extracted with ethyl acetate, then organic phases were merged and washed successively with water and saturated salt water, dried by anhydride Na2SO4, concentrated to give the crude product, mixed and purified by column chromatograNHphy (eluent was ethyl acetate:petroleum ether= 10:1 5: 1),and light yellow solid lc was obtained (365 mg, 65% yield)EC-MS: 562 [M+l]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | at 120℃; for 2h; | 11 g of [ChCl] [NiCl2.6H2O] eutectic solvent and 14.4 g(0.10 mol) octanoic acid were mixed with 6.02 g (0.01 mol)Ethylene glycol into the reactionbottle,Stirring,The control temperature is 120 ,The reaction was carried out for 2 hours,Take 1 muL sample into the sample,The yield of octyl acetate in the reactants was determinedby gas chromatography,The column was HP5MS.The specific test conditions are: chamber temperature 140 ,Gasification chamber 320 C,Detection chamber 320 .The reaction selectivity was determined by a FinniganTraceDSQ GC-MS,The column used was HP5MS.The conversion of ethylene octanoate under the abovereaction conditions was 90%Selectivity is 100%.The reaction solution was allowed to stand,The upper organic phase obtained by the separation was theethyl ester of the esterification reaction product.The low-temperature eutectic solvent of the lower layer canbe reused after simple water removal. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 17% 2: 66% | With Mo(Oxo)/C at 90℃; for 2h; Inert atmosphere; | 26 Example 26 General procedure: [0148] To extend the study summarized in Table 4, transesterification in the presence of H20 (0 to 1 equiv) did not diminish the catalytic activity at 90° C., indicating the MoC catalyst is not poisoned under these conditions. No reaction occurs in the absence of catalyst or with the activated carbon support alone (Table 11, entries 1 and 2). In a control study with n-octyl acetate at 90° C. in dry EtOH, MoO3 is found to exhibit some activity; however, under the same conditions, the yield (mmol product/mol Mo h’) is 5.8x higher for MoC, confirming the high activity of the carbon-supported dioxo-Mo species. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 23% 2: 30% 3: 10% 4: 7% 5: 9% | With C15HBBr3F18N6(1-)*Ag(1+)*C4H8O In water at 20℃; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27%Chromat.; 8%Chromat.; 7%Chromat. | With oxygen; at 100℃; under 3750.38 Torr; for 5h;Autoclave; | General procedure: Octanal (128 mg, 1.00 mmol), ethanol (2 mL, 34.3 mmol), 1 wt% gold catalyst (100 mg, Au 0.5 mol%), tridecane as an internal standard, and a magnetic stirring bar was charged in an autoclave. Oxygen gas was filled in the autoclave with 0.5 MPa (the gauge pressure). The reaction was carried out at 100 C. After 5 h, the reaction mixture was extracted with ethanol and filtered. The filtrate was analyzed by gas chromatography using an Agilent7890A or a Shimadzu GC2014 with an HP-5 column. |
8%Chromat.; 13%Chromat.; 58%Chromat. | With oxygen; at 100℃; under 3750.38 Torr; for 5h;Autoclave; | General procedure: Octanal (128 mg, 1.00 mmol), ethanol (2 mL, 34.3 mmol), 1 wt% gold catalyst (100 mg, Au 0.5 mol%), tridecane as an internal standard, and a magnetic stirring bar was charged in an autoclave. Oxygen gas was filled in the autoclave with 0.5 MPa (the gauge pressure). The reaction was carried out at 100 C. After 5 h, the reaction mixture was extracted with ethanol and filtered. The filtrate was analyzed by gas chromatography using an Agilent7890A or a Shimadzu GC2014 with an HP-5 column. |
63%Chromat.; 6%Chromat.; 12%Chromat. | With oxygen; at 100℃; under 3750.38 Torr; for 5h;Autoclave; | General procedure: Octanal (128 mg, 1.00 mmol), ethanol (2 mL, 34.3 mmol), 1 wt% gold catalyst (100 mg, Au 0.5 mol%), tridecane as an internal standard, and a magnetic stirring bar was charged in an autoclave. Oxygen gas was filled in the autoclave with 0.5 MPa (the gauge pressure). The reaction was carried out at 100 C. After 5 h, the reaction mixture was extracted with ethanol and filtered. The filtrate was analyzed by gas chromatography using an Agilent7890A or a Shimadzu GC2014 with an HP-5 column. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6%Chromat.; 92%Chromat. | With oxygen; at 100℃; under 3750.38 Torr; for 5h;Autoclave; | General procedure: Octanal (128 mg, 1.00 mmol), ethanol (2 mL, 34.3 mmol), 1 wt% gold catalyst (100 mg, Au 0.5 mol%), tridecane as an internal standard, and a magnetic stirring bar was charged in an autoclave. Oxygen gas was filled in the autoclave with 0.5 MPa (the gauge pressure). The reaction was carried out at 100 C. After 5 h, the reaction mixture was extracted with ethanol and filtered. The filtrate was analyzed by gas chromatography using an Agilent7890A or a Shimadzu GC2014 with an HP-5 column. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29%Chromat.; 19%Chromat. | With oxygen; at 100℃; under 3750.38 Torr; for 16h;Autoclave; | General procedure: Octanal (128 mg, 1.00 mmol), ethanol (2 mL, 34.3 mmol), 1 wt% gold catalyst (100 mg, Au 0.5 mol%), tridecane as an internal standard, and a magnetic stirring bar was charged in an autoclave. Oxygen gas was filled in the autoclave with 0.5 MPa (the gauge pressure). The reaction was carried out at 100 C. After 5 h, the reaction mixture was extracted with ethanol and filtered. The filtrate was analyzed by gas chromatography using an Agilent7890A or a Shimadzu GC2014 with an HP-5 column. In the case of oxidative esterification of 1-octanol with ethanol, the reaction was carried out using 1-octanol (130 mg, 1.00 mmol) instead of octanal for 16 h. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: octanoic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil for 0.166667h; Cooling with ice; Stage #2: ethyl 3,4,5-trimethoxybenzoate In tetrahydrofuran; mineral oil Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.43% | Stage #1: methanol; 1-bromo-butane; octanoic acid ethyl ester With sodium hydroxide at 20 - 55℃; for 7h; Large scale; Stage #2: With water; sodium carbonate at 70℃; for 6h; Large scale; | 2.S1-2.S3 Example 2 A synthesis method of Guerbet acid includes the following steps: S1, at 2030,Dissolve 1000g of ethyl octoate and 513.56g of sodium hydroxide in 5000g of methanol and add it to the reactor.Then slowly add 954.51g bromo-n-butane,After the addition is completed, the temperature is raised to 55°C for 7h; S2. Dissolve 922.94g sodium carbonate in 417.97g water and slowly add it to the reaction tank.Incubate at 70 for 6h,Remove the solvent by distillation under reduced pressure; S3, drop to room temperature,Add 1mol/L hydrochloric acid solution to neutralize the system pH=34,Allow to stand, separate, and the organic phase is dissolved in 1000mL petroleum ether,Add 2000mL water to wash twice, add 11.63g activated carbon to decolor,The low boiling point component was distilled off under reduced pressure at 80°C to obtain 1063.23g of colorless transparent liquid.It is 2-butyloctanoic acid with a yield of 91.43% and a purity of >98%. |
Tags: 106-32-1 synthesis path| 106-32-1 SDS| 106-32-1 COA| 106-32-1 purity| 106-32-1 application| 106-32-1 NMR| 106-32-1 COA| 106-32-1 structure
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Code | Phrase |
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H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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