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CAS No. : | 6920-22-5 | MDL No. : | MFCD00010737 |
Formula : | C6H14O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FHKSXSQHXQEMOK-UHFFFAOYSA-N |
M.W : | 118.17 | Pubchem ID : | 94335 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 33.28 |
TPSA : | 40.46 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) : | -6.51 cm/s |
Log Po/w (iLOGP) : | 1.66 |
Log Po/w (XLOGP3) : | 0.72 |
Log Po/w (WLOGP) : | 0.53 |
Log Po/w (MLOGP) : | 0.61 |
Log Po/w (SILICOS-IT) : | 0.61 |
Consensus Log Po/w : | 0.82 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.76 |
Solubility : | 20.4 mg/ml ; 0.173 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.15 |
Solubility : | 8.4 mg/ml ; 0.0711 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.73 |
Solubility : | 21.9 mg/ml ; 0.185 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.78 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
90.4% | With formic acid; 3C38H80N(1+)*O16PW4(3-); dihydrogen peroxide; In water; at 25℃; for 2h;Green chemistry; | General procedure: The catalytic reactions were performed in a 50 mL four-necked round-bottomed flask equipped with a reflux condenser. The assembly was kept in an isothermal water bath at a constant known temperature and mechanically agitated with an electric motor. The oxidation was carried out as follows: catalyst (0.12 mmol), terminal alkenes (30 mmol), H2O2 (30% aq., 40 mmol) and FA (60 mmol) were charged in the reaction flask. The catalyst/olefin ratio was 1:250 for all the reactions. When the oxidation reaction was over, the catalyst was precipitated from the reaction medium for further use when acetone was subsequently added to the solution, the precipitate was removed by centrifugation and filtration, and the filtrate extracted with CH2Cl2 (50 mL×3); the organic layer was collected and dried under anhydrous Na2SO4. After the evaporation of the solvent under reduced pressure, a solution of sodium hydroxide was added dropwise to the organic product to give high purity 1,2-diols. The organic product was analyzed by GC9600 using an internal standard method. Typical GC-MS analysis was also conducted to identify the products. |
89% | In a 100 L reactor, add 34 kg of water, 16 kg of acetone,35kg potassium peroxodisulfate complex salt (oxone, 0.0569Kmol),Sodium chloride 3.4kg (0.058Kmol) and1-hexene5kg (0.059Kmol), heated to 50 C, stirred for 18h, after the reaction is completed, the temperature is lowered to 25 C, 20% aqueous sodium hydroxide solution is added to adjust the pH to 12, heated to 50 C,The reaction was stirred for 3 h.After the reaction, the temperature was lowered to room temperature, and the alkalinity was maintained. The impurities were removed by dichloromethane extraction, and then the pH was adjusted to 2 with 6 mol/L hydrochloric acid. The product was extracted with ethyl acetate, and the solvent was evaporated.There was obtained 6.24 kg of 1,2-hexanediol, and the yield was 89%. | |
85% | With 4-methylmorpholine N-oxide; In water; acetone; at 20℃; for 4h;Inert atmosphere; | General procedure: A mixture of alkene (250 mol), 5% Os/CR11 (9.5 mg, 2.50 mol, 1 mol%), NMO (32.2 mg, 275mol), and acetone-H2O (7 : 3, 0.5 mL) in a 15 mL-test tube was stirred under an Ar atmosphere atroom temperature. After the specific time [the consumption of the starting material was confirmedby TLC analysis (hexane-EtOAc)], the mixture was filtered through a Celite pad, and the pad waswashed with acetone (30 mL) and concentrated in vacuo. The residue was purified by columnchromatography on silica gel (hexane-EtOAc) to give the corresponding diol |
85.5% | With Perbenzoic acid; In dichloromethane; at 50 - 60℃; for 3h;Large scale; | A 1,2-hexanediol gas-liquid pipeline preparation method specific steps are as follows: The pipe-type reactor is provided with two feed ports ,A feed inlet 1, a feed inlet 2, Connecting the feed inlet 1 There is a pipe reactor with agitation; Benzoate (commercially available) were dissolved in 882 kg of methylene chloride, From the feed port 1 into the pipeline, 252 kg of 1-hexene was introduced into the feed port 2, Heated to 50 C to 60 C, Incubation reaction 3 hours, Sampling TLC (developing solvent ethyl acetate:Ethanol = 4: 1) detection, To 1-hexene.Cooling to 20 ~ 30 , adding ammonia and open-loop generated 1,2-hexanediol reaction solution, From the export of materials to the reactor for post-processing, Continue to feed raw materials from the feed port; Reaction post-treatment, The reaction solution was adjusted to pH 7 with industrial hydrochloric acid, 800 kg of methyl tert-butyl ether, Stirred for 30 minutes, Standing stratification, The upper layer is an organic layer (product) The lower layer is a water layer, and the aqueous layer is extracted twice with 80 kg of methyl tert-butyl ether, The organic layers were combined, The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off. Vacuum distillation, The top temperature was 128 C to 132 C / 680 KPa, To give 302.7 kg of 1,2-hexanediol, Product content of 99.5% The yield was 85.5% based on 1-hexene. |
EXAMPLE 5 The conditions of Example 4 were repeated except that 2.2 grams of 1-hexene were used instead of cyclohexene. After four hours of reaction time, titration showed that 0% of the starting peroxide remained. GC-MS analysis indicated a single oxidation product, 1,2 hexanediol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium aluminium tetrahydride; diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With potassium bromate; potassium hydrogensulfate; In water; at 20℃; for 24h;Darkness; | General procedure: To a solution of 1,2-diol 1a (1.0 mmol) in water (4 mL), KBrO3 (0.5 mmol) was added followed by addition of KHSO4 (1.0 mmol). The reaction was conducted at room temperature under shielding from light until 1a disappeared, as monitored by TLC. After the reaction completion, aqueous saturated Na2S2O3 solution(10 mL) was added. The organic portion was extracted with AcOEt (3 40 mL)and then dried over MgSO4. The solvent was removed under vacuum and the residue was subjected to silica gel column chromatography (n-hexane/AcOEt5:1) to afford (134 mg, 94% yield) of product 2a. |
79%Spectr. | With (2,9-dimethyl-1,10-phenanthroline)-palladium(II) acetate; 2,6-dimethoxy-p-quinone; tetrabutylammonium tetrafluoroborate; acetic acid; In dimethyl sulfoxide; at 20℃; for 8h;Electrolysis; Inert atmosphere; | General procedure: A homemade airtight electrolysis cell was used equipped with areticulated vitreous carbon (RVC) as working electrode (basi, USA),a bridged Ag/AgCl reference electrode with 2 M LiCl ethanol solution as inner solution and a 0.1 M Bu4NBF4 DMSO as bridge solution was used and the counter electrode, a platinum rod electrode, was put in a divided cell separated from the anodic partby a ceramic frit. In a typical electrolysis experiment 4 mL of a 0.2 MBu4NBF4 DMSO solution was added to the divided part followed bythe addition of 200 mL of acetic acid. In the anodic part neocuproinePd(OAc)2 (0.1 equivalent), 2,6-dimethoxybenzoquinone(0.6 equivalent) and the alcohol (0.7 mmol) was added to a 14 mL solution of 0.2 M Bu4NBF4 in DMSO. The cell was closed andput under an argon atmosphere. Stirring was started, next apotential of 0.7 V was applied. After the appropriate reaction time30 mL of water was added to the reaction mixture. The resultingmixture was extracted with tert-butylmethylether (3 times 25 mL).The collected organic layer was washed with 15 mL of water tofurther remove DMSO. Next the organic layer was dried withMgSO4 filtered and evaporated. The resulting solution wasexamined with NMR. Isolated products were obtained usingcolumn chromatography with heptane/ethylacetate (7/3) aseluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With toluene-4-sulfonic acid In benzene | |
97% | With toluene-4-sulfonic acid In benzene at 120℃; for 14h; | |
97% | With toluene-4-sulfonic acid In benzene at 120℃; for 14h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With dmap; triethylamine; In dichloromethane; at 20℃; for 16h;Cooling with ice; | Add 3.6 mL of 1,2-hexanediol, 15 mL of triethylamine, 30 mg of dimethylaminopyridine in a 200 mL round bottom bottle.Acridine, 100 mL of dichloromethane, and 10 mL of acetic anhydride were slowly added dropwise while stirring in an ice bath. After the addition is completed, the ice bath is removed and the system is at normal temperature.Stir for 16 hours. The reaction solution was washed with water, 1N hydrochloric acid and saturated sodium chloride solution, dried over anhydrous sodium sulfateObject. Finally, the product 1n was obtained by column chromatography (petroleum ether: ethyl acetate = 10:1).The isolated yield was 72%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With dihydrogen peroxide; sodium hydroxide; In water; at 79.84℃; for 8h;Schlenk technique; | General procedure: All experiments to test the catalytic activity were performed in a Schlenk tube (50mL vol.) attached to a condenser. The catalytic activity was evaluated for HDO oxidation in basic aqueous media with H2O2 as oxidant to obtain HCA. In a typical reaction procedure, aliphatic diol (0.5mmol) and catalyst (25mg) were weighed and dispersed in deionized water (3.5mL) in a Schenk tube. 30% H2O2 (0.75mL) and 0.5M NaOH (0.75mL) were added to the above mixture, and then the Schlenk tube was mounted on a preheated oil bath at 353K. The mixture was allowed to react for various time intervals with continuous magnetic stirring (500 rpm). After the reaction, a part of the resultant solution was diluted 20 times with an aqueous H2SO4 (10mM) solution, and the catalyst was filtered off using a 0.20mum filter (Milex-LG). The obtained filtrate was analyzed by high performance liquid chromatography (HPLC, WATERS 600) using an Aminex HPX-87H column (Bio-Rad Laboratories, Inc.) attached to a refractive index detector. An aqueous 10mM H2SO4 solution (eluent) was run through the column (maintained at 323K) at a flow rate of 0.5mLmin-1. The conversion and yield(s) were determined with a calibration curve method using commercial products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With cesiumhydroxide monohydrate; In toluene; at 150℃; for 24h;Inert atmosphere; Sealed tube; | General procedure: To an oven dried 9mL screw cap tube, a magnetic stir-bar, diamine (0.5mmol), vicinal diol (1.5mmol), CsOH.H2O (0.375mmol), Co-phen/C-800 (1.5mol%) and toluene (2.5mL) were added under argon atmosphere. Then, the tube was sealed and placed in a preheated oil bath at 150C for 24h. After completion of the reaction, the tube was allowed to cool at room temperature. Then, the solvent was evaporated under reduced pressure. Finally, the product was purified by silica gel column chromatography using ethyl acetate/hexane as eluent. |
81% | In diethylene glycol dimethyl ether; at 140℃; for 24h; | A generic experiment was as follows. In a two-neck roundbottomflask of 10 mL, 1,2-phenylenediamine (1a, 0.5 mmol),1,2-propyleneglycol (2a, 0.6 mmol), 1.5 mL of diethylene glycol dimethylether (diglyme), and an amount of catalyst were added.Subsequently, the reaction mixture was heated at 140 C in a siliconebath that contains a magnetic stirrer and a temperature controller. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A 500 mL three-necked round-bottom flask equipped with mechanical stirrer, pressure equalizing addition funnel, and reflux condenser is charged with 1,2-hexanediol (6, 5.91 g, 50.0 mmol) and 50 mL of carbon tetrachloride. Upon dissolving of the 1,2-hexanediol, thionyl chloride (5.5 mL, 75 mmol) is added dropwise at room temperature, and the reaction is heated to 60 C. After 2 h, the reaction is cooled via ice bath. Water (50 mL) and acetonitrile (75 mL) are added. Ruthenium chloride hydrate (0.131 g, 0.50 mmol) and sodium periodate (21.4 g, 100 mmol) are added and the reaction mixture is stirred at room temperature for I h. The mixture is extracted with diethyl ether (4 x 175 mL), the organic layers are washed with water (5 x 100 mL), saturated sodium bicarbonate (3 x 100 mL), brine (2 x 100 mL), filtered through celite/silica gel, and dried over magnesium sulfate. The clear liquid is concentrated to give 7, a clear oil. The preparation is represented by the following reaction: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | 248 g Triacetonamin wurden zusammen mit 378 g 1,2-Hexandiol in 500 ml Toluol vorgelegt. Anschliessend wurde ueber ein Tauchrohr Chlorwasserstoffgas in den Reaktor eingeleitet, wobei die Sumpftemperatur unter 80 C gehalten wurde. Sobald die Chlorwasserstoff-Aufnahme deutlich nachliess, wurde das Reaktionsgemisch auf Rueckflusstemperatur erhitzt und das entstandene Reaktionswasser am Wasserabscheider ausgekreist. Sobald vollstaendiger TAA-Umsatz erreicht war, liess man das Reaktionsgemisch abkuehlen und stellte durch Zugabe von 303 g 25 %iger NaOH-Loesung und 76 g Wasser einen pH-Wert von 11 ein. Nach Trennung der Phasen wurde die waessrige Phase 3 mal mit Toluol extrahiert. Die vereinigten organischen Phasen wurden fraktioniert im Vakuum destilliert. Ausbeute: 322 g (79 %), Siedepunkt: 92 C/0,5 mbar. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.8% | toluene-4-sulfonic acid; In water; toluene; at 140℃; for 4.5h;Heating / reflux; with Dean-Stark tube; | Example 1[ Synthesis of vanillin-1 , 2-hexylene glycol acetal ( compound A) ]( Compound A ) EPO <DP n="30"/>Into a 300 ml reaction flask with a thermometer, a Dean-Stalk tube and a refluxing tube, 25.0 g of vanillin (molecular weight 152.14, 164.31 mmol) , 21.36 g of hexylene glycol (molecular weight 118.18, 180.74 mmol), 150 mg of p-toluenesulfonic acid monohydrate (molecular weight 190.22, 789 mumol) , and 150 ml of toluene were charged, and the mixture was heated and refluxed in an oil bath at 14O0C under nitrogen current. While removing formed water through the Dean-Stalk tube,' the mixture was continuously refluxed. After heated for 4.5 hours, disappearance of raw materials was confirmed by the gas chromatogram. The reaction solution obtained was quenched in an aqueous sodium carbonate solution, extracted with toluene, washed with salt water, and dried with dehydrated sodium sulfate . After filtration, the solvent in the extract solution was removed by a rotary evaporator and then subj ected to vacuum distillation to obtain an aimed compound, vanillin-1, 2-hexylene glycol acetal (molecular weight 252.31), in form of a colorless transparent oil . The production amount was39.73g (157.47 mmol) ; the purity was 100% (isomer ratio 54.3 : 43.7); the yield was 95.8%; and the boiling point was 127 to 1290C (9 to 15 Pa).1H-NMR (500MHz, CDCl3, delta) ppm: 0.90-0.94 (m, 3H) , 1.32-1.42 (m, 2H), 1.52-1.62 (m, 2H), 3.46-3.57 (m,2H) ,3.51-3.66 (m, 2H) , 3.80-3.99 (m, IH), 4.07-4.28 (m, IH), 4.33-4.45 (m, IH), 3.80-3.99 (m, IH), 5.76-5.86 (m, 2H), 6.88-6.92 (m, IH), 6.96-7.02 (m, 2H).IR cm"1: 3501, 3077, 2961, 2873, 1657, 1472, 1455, 1414, EPO <DP n="31"/>1369, 1259, 1171, 1093, 1032, 992, 899.MS (m/e) : 200(M"), 183, 167, 157, 145, 128, 110, 95, 85, 83, 73, 55, 43, 29. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium tert-butylate; hydrogen; C39H37N2OP2Ru(1+)*Cl(1-); In tetrahydrofuran; at 140℃; under 38002.6 Torr; for 24h;Glovebox; Autoclave; | General procedure: In the glove box,To a 125 mL autoclave, add ruthenium complex 1a (7.5 mg, 0.01 mmol), potassium tert-butoxide (2.3 mg, 0.02 mmol), tetrahydrofuran (20 mL),Cyclic carbonate (20 mmol).After sealing the autoclave, remove it from the glove box,Fill with 50atm hydrogen. The reaction kettle was heated and stirred in a 140C oil bath for a specific period of time. After cooling the reaction kettle in an ice water bath for 1.5 hours, the excess hydrogen was slowly released.With p-xylene as the internal standard, use gas chromatography (using the standard curve method, that is, with p-xylene as the internal standard, for cyclic carbonate,Methanol and diol are used as standard curves on the gas chromatography with the ratio of the peak area to the peak area of para-xylene. By measuring the ratio of the peak area in the reaction system, the cyclic carbonate contained in the reaction system mixture after the reaction is determined , The quality of methanol and glycol.The same gas chromatography method as in Example 9 was used to determine the conversion of cyclic carbonate and the yield of methanol and diol. The results are shown in Table 6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | With ammonium metavanadate; In 2,2,2-trifluoroethanol; at 225 - 235℃; under 11251.1 Torr; for 16.6667h;Autoclave; Inert atmosphere; Sealed tube;Catalytic behavior; | Example 1 - Deoxydehyd ration of 1,2-decanediol In the following examples, unless something else is stated, 40 mmol of diol, 2.0 mmol of catalyst (5 mol%, calculated with respect to the amount of vanadium), 500 mg of hexadecane (internal standard), and 100 ml of solvent were mixed in a 300 ml PTFE cup and placed in a 400 ml autoclave with a magnetic stir bar and computer-controlled heating plate. The autoclave was sealed, pressurized with 10-25 bar of H2, N2, or CO and heated to 230 C for 1000 min (corresponding to ~ 16 h at the reaction temperature); the temperature typically stabilized between 225 and 235 C. When the system had cooled to room temperature, the pressure was released, the reaction mixture was filtered to remove a black precipitate and analyzed by GC (for determination of conversion and yields) and GC-MS (for observation and identification of other products). Comparison of solvents A number of primary or secondary monohydric Ci-Cio alcohol solvents were tested together with NH4V03 as the catalyst. In addition, their performance was compared to that of acetone and hexane as solvents. The yields of 1-decene (C=C), 2-decanone (C=0), 2-decanol (2OH), and 1-decanol (lOH) are provided below in Table 1. It is evident that using a primary or secondary monohydric Ci-Cio alcohol as the solvent results in a better selectivity of 1-decene than any of the comparative solvents. |
10%Chromat. | With 5-nonanol; methyltrioxorhenium(VII); In dodecane; benzene; at 140℃; for 48h;Sealed tube; | General procedure: CH3ReO3 (0.036 mmol), Glycol (0.36 mmol) and and 0.022 mmol dodecane (internal standard), 5-nonanol (0.68 mmol) were mixed in anhydrous benzene (2 mL) in a 1.5 mL thick walled glass tube fitted with Teflon screw-cap/plunger (Ace Glass), and a spin bar was added. The reaction mixture was heated at 90-150 C in a preheated oil bath for 24-95 h. The mixture was cooled to room temperature, and an aliquot removed for GC-MS analysis. |
45%Chromat. | With hexaammonium heptamolybdate tetrahydrate; at 190 - 220℃; | Example 3 - Deoxydehydration in 1,5-pentanediol A mixture of 0.030 mol of polyol (1,2-hexanediol or glycerol) was mixed with 2.5 mol% of (NuEta4)6Mutheta7theta24-4Eta20 and 10 g of 1,5-pentanediol in a round-bottomed flask fitted with a distillation setup. The mixture was heated to 190-220 C until no more volatile products distilled, and the distillate was analyzed by GC. |
9%Chromat. | With ammonium perrhenate; 2,4-dimethyl-3-pentanol; In toluene; at 165℃; for 24h;Sealed tube; | General procedure: Glycerol (0.3 mmol, 42 mg), NH4ReO4 (0.03 mmol, 8 mg), 2,4-dimethyl-3-pentanol (0.43-0.86 mmol, 60-120 muL), and 1 mL anhydrous toluene were added to a thick-walled Ace glass reactor tube. The Teflon seal was closed and the reactor was placed in a heating mantle connected with a Digi Troll (Glas-Col) digital temperature controller equipped with a thermocouple at 140-165 C for 5-48 h while stirring. After cooling to room temperature, the solution was filtered to remove the precipitated NH4ReO4 and analyzed with GC-MS |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 3 % platinum on carbon; hydrogen In water at 179.84℃; for 2h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With dibutyltin chloride; tetrabutylammomium bromide; potassium carbonate; In N,N-dimethyl-formamide; acetonitrile; at 80℃; for 3h; | General procedure: Diol or polyol (100mg) and dibutyltin dichloride (0.1 equiv) were added in dry MeCN/DMF (10:1) (2 mL), in the presence of TBAB (0.1 equiv), K2CO3 (1.5 equiv) and alkylation reagent (2.0 equiv). The reaction proceeded at 80C for 3 h. After the removal of the solvents, the residue was purified by column chromatography to give the desired pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With dibutyltin chloride; tetrabutylammomium bromide; potassium carbonate; In N,N-dimethyl-formamide; acetonitrile; at 80℃; for 3h; | General procedure: Diol or polyol (100mg) and dibutyltin dichloride (0.1 equiv) were added in dry MeCN/DMF (10:1) (2 mL), in the presence of TBAB (0.1 equiv), K2CO3 (1.5 equiv) and alkylation reagent (2.0 equiv). The reaction proceeded at 80C for 3 h. After the removal of the solvents, the residue was purified by column chromatography to give the desired pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen; sodium hydroxide; In water; at 210℃; under 45004.5 Torr; for 2h;Autoclave; | General procedure: The hydrogenolysis of sorbitol was performed in a 50 mL stainless-steel autoclave with magnetic stirring. After sorbitol aqueous solution, Ru catalyst and an appropriate amount of basewere charged into the reactor, the autoclave was purged with hydrogen four times and then pressurized to the desired pressure at room temperature. Then the reaction was performed atcertain temperature under the stirring speed of 800 r/min. After the reaction, the reactor was cooled down and the used catalystwas separated from the reaction mixture by centrifugation. Thesamples were filtered through 0.22 m-pore-size filters (Mem-brana) prior to analysis. The obtained products such as 1,2-PG,EG and GLY were determined using a gas chromatography (GC,7890A, Agilent, USA) equipped with a CP-Wax 58 (FFAP) capillarycolumn (0.25 mm × 25 m) and a flame ionization detector. Otherproducts like glucose, sugar alcohols were quantified by Anion-Exchange Chromatography (IC, Dionex ICS-3000) equipped with pulsed amperometric detector and an Aminex HPX-87H column(Bio-Rad, 7.8 × 300 mm), using 500 mM NaOH as eluent with a flowrate of 0.4 mL min-1at 30C. The obtained products in resultant solutions were also identified by GC-MS (6890N, Agilent, USA). The conversion of sorbitol and yields of products were calculated on the carbon basis and defined as follows |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen; sodium hydroxide; at 210℃; under 45004.5 Torr; for 2h; | General procedure: The hydrogenolysis of sorbitol was performed in a 50 mL stainless-steel autoclave with magnetic stirring. After sorbitol aqueous solution, Ru catalyst and an appropriate amount of basewere charged into the reactor, the autoclave was purged with hydrogen four times and then pressurized to the desired pressure at room temperature. Then the reaction was performed atcertain temperature under the stirring speed of 800 r/min. After the reaction, the reactor was cooled down and the used catalystwas separated from the reaction mixture by centrifugation. Thesamples were filtered through 0.22 m-pore-size filters (Mem-brana) prior to analysis. The obtained products such as 1,2-PG,EG and GLY were determined using a gas chromatography (GC,7890A, Agilent, USA) equipped with a CP-Wax 58 (FFAP) capillarycolumn (0.25 mm × 25 m) and a flame ionization detector. Otherproducts like glucose, sugar alcohols were quantified by Anion-Exchange Chromatography (IC, Dionex ICS-3000) equipped with pulsed amperometric detector and an Aminex HPX-87H column(Bio-Rad, 7.8 × 300 mm), using 500 mM NaOH as eluent with a flowrate of 0.4 mL min-1at 30C. The obtained products in resultant solutions were also identified by GC-MS (6890N, Agilent, USA). The conversion of sorbitol and yields of products were calculated on the carbon basis and defined as follows |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.9% | With copper chromite; 2-(N,N-dimethylamino)athanol; 5,10,15,20-tetraphenyl-21H,23H-porphine; 1-(1-ferrocenylethyl)-3-isopropyl-imidazolium iodide salt; nickel dichloride; In 1,4-dioxane; at 70℃; for 12h; | At room temperature, to the right amount of organic solvent (volume ratio 4:1 of the 1,4-dioxane and polyethylene glycol 200 (PEG-200) mixture), add 100mmol said formula (I) compound, 150mmol said formula (II) compound, 140mmol said formula (III) compound, 10mmol catalyst (2mmol 1-(1-ferrocenylethyl)-3-isopropyl-1-imidazolium iodide and 8mmol nickel chloride mixture), 200mmol oxidant copper chromite (Cr2Cu2O5), 120mmol base N,N-dimethylethanolamine (DMEA) and 10mmol promoter tetraphenylporphyrin, then heat up to 70 C, and at this temperature the stirring reaction 12 hours;After the reaction, the filtering net filtering, the filtrate pH value is adjusted to the neutral, and then saturated sodium carbonate aqueous solution for washing, adding acetone extraction of 2 - 3 times, the combined organic phase, concentrated under reduced pressure, the residue over 300 - 400 mesh silica gel column chromatography, for the volume ratio of 1:2 of the mixture of ethyl acetate and petroleum ether elution, so as to obtain the compound of formula (IV), and the yield is 92.9%. |
71.2% | With 2-(N,N-dimethylamino)athanol; copper chromite; 1-(1-ferrocenylethyl)-3-isopropyl-1-imidazolium iodide; nickel dichloride; In 1,4-dioxane; at 80℃; for 10h; | At room temperature, to a solution of an appropriate amount of an organic solvent (a mixture of 1,4-dioxane and polyethylene glycol 200 (PEG-200) in a volume ratio of 4: 1)100 mmol of the compound of formula (I)200 mmol of the compound of formula (II)120 mmol of the compound of formula (III)15 mmol of a catalyst (a mixture of 3 mmol of 1- (1-ferrocenylloxy) -3-isopropyl-1-imidazolium iodide and 12 mmol of nickel chloride)170 mmol oxidant copper chromite (Cr2Cu2O5)And 150 mmol of alkali N, N-dimethylethanolamine (DMEA)Then heated to 80 C,And the reaction was stirred at that temperature for 10 hours;After the reaction,Buchner funnel suction filter,The pH of the filtrate was adjusted to neutral,Washed with saturated aqueous sodium carbonate solution,Add acetone extraction 2-3 times,Combine organic phase,Concentrated under reduced pressure,The residue was passed through a 300-400 mesh silica gel column chromatography,With a 1: 2 by volume mixture of ethyl acetate and petroleum ether,Thereby obtaining a compound of the above formula (IV)N-C4H9 is n-butyl),The yield was 71.2%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.5% | Stage #1: Hexane-1,2-diol With tetrabutoxytitanium at 120℃; for 2h; Stage #2: dimethylsulfite at 64 - 150℃; | 2 Example 3 4-Butyl Sulfite With the condenser,Stirring and thermometer in a three bottle,Add 1000g 1,2-hexanediol and 15g anhydrous sodium sulfate,The reaction was performed at 130 °C for 2 hours.To prevent the entry of water vapor in the air,Drying pipe on the top of the condenser,Anhydrous magnesium sulfate was added to the drying tube.Then vacuum quickly filter,The moisture content was measured with a trace moisture meter of 180 ppm.When equipped with a stirrer,thermometer,In the three-port bottle of the fractionation tower,594 g of dried 1,2-hexanediol was added,Add 11g tetrabutyl titanate,Reaction at 120°C for 2 hours,Then add 550g dimethyl sulfite,The reaction starts at 120°C in the oil bath.And by controlling the oil bath temperature does not exceed 150 °C,Maintain the fractionation tower top temperature at 64-67°C.When the oil bath temperature is 150°C,The distillation tower no longer has a methanol distillate.Stop the reaction.Changed to a vacuum distillation unit,The degree of vacuum is maintained at -0.095 MPa.Collect 100-102 °C fractions,Obtained 750 g of 4-butyl sulfite (structure 3),Yield 91.5%, purity: 99% (HPLC). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With cesiumhydroxide monohydrate; In toluene; at 150℃; for 24h;Inert atmosphere; Sealed tube; | General procedure: In an oven dried 9mL screw cap tube a magnetic stir-bar, nitroamine (0.5mmol), vicinal diol (2.5mmol), CsOH.H2O (0.125mmol), Co-phen/C-800 (1.5mol%) and toluene (2.5mL) were added under argon atmosphere. Then, the tube was sealed and placed in a preheated oil bath at 150C for 24h. After completion of the reaction, the tube was allowed to cool at room temperature. Next, the solvent was evaporated under reduced pressure. Finally, the quinoxaline was purified by silica gel column chromatography using ethyl acetate/hexane as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67%Chromat.; 98% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride; In acetonitrile; at 80℃; under 7500.75 Torr; for 24h;Autoclave; Sealed tube; | General procedure: A 50-mL stainless steel autoclave equipped with a magnetic stir bar was charged with ZnCl2 (27.2 mg, 20 mol%), DBU (76 mg, 50 mol%), 4a (76.1 mg, 1 mmol), 2a (126.1 mg, 1.5 mmol), and CH3CN (2.0 mL) successively and sealed at r.t. The pressure was adjusted to 1 MPa with CO2 at the preset temperature (80 C) and the autoclave was heated at this temperature for 24 h. After the reaction was complete, the reactor was cooled in ice-water bath, and then excess CO2 was carefully vented. The mixture was diluted with EtOAc, and the yield of cyclic carbonate 5a and alpha-hydroxy ketone 6a was determined by gas chromatograph (Agilent 6890) equipped with a capillary column (HP-5 30 m * 0.25 mum) using a flame ionization detector using biphenyl (40 mg) as the internal standard. Then, the residue was obtained by removing the solvent under vacuum and further purified by column chromatography (petroleum ether/EtOAc 100:1-5:1) to obtain 5a and 6a. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With cesiumhydroxide monohydrate; In toluene; at 150℃; for 36h;Inert atmosphere; Sealed tube; | General procedure: In an oven dried 9mL screw cap tube a magnetic stir-bar, nitroamine (0.5mmol), vicinal diol (2.5mmol), CsOH.H2O (0.125mmol), Co-phen/C-800 (1.5mol%) and toluene (2.5mL) were added under argon atmosphere. Then, the tube was sealed and placed in a preheated oil bath at 150C for 24h. After completion of the reaction, the tube was allowed to cool at room temperature. Next, the solvent was evaporated under reduced pressure. Finally, the quinoxaline was purified by silica gel column chromatography using ethyl acetate/hexane as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With cesiumhydroxide monohydrate; In toluene; at 150℃; for 36h;Inert atmosphere; Sealed tube; | General procedure: To an oven dried 9mL screw cap tube, a magnetic stir-bar, diamine (0.5mmol), vicinal diol (1.5mmol), CsOH.H2O (0.375mmol), Co-phen/C-800 (1.5mol%) and toluene (2.5mL) were added under argon atmosphere. Then, the tube was sealed and placed in a preheated oil bath at 150C for 24h. After completion of the reaction, the tube was allowed to cool at room temperature. Then, the solvent was evaporated under reduced pressure. Finally, the product was purified by silica gel column chromatography using ethyl acetate/hexane as eluent. |
Tags: 6920-22-5 synthesis path| 6920-22-5 SDS| 6920-22-5 COA| 6920-22-5 purity| 6920-22-5 application| 6920-22-5 NMR| 6920-22-5 COA| 6920-22-5 structure
[ 13074-06-1 ]
(2R,3S,4R,5S)-Hexane-1,2,3,4,5-pentaol
Similarity: 0.92
[ 13074-06-1 ]
(2R,3S,4R,5S)-Hexane-1,2,3,4,5-pentaol
Similarity: 0.92
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