Alternatived Products of [ 6126-49-4 ]
Product Details of [ 6126-49-4 ]
| CAS No. : | 6126-49-4 |
MDL No. : | MFCD00010085 |
| Formula : |
C6H12O2
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
116.16
|
Pubchem ID : | - |
| Synonyms : |
|
Safety of [ 6126-49-4 ]
| Signal Word: | |
Class: | |
| Precautionary Statements: | |
UN#: | |
| Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 6126-49-4 ]
* 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.
- Downstream synthetic route of [ 6126-49-4 ]
- 1
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[ 10551-58-3 ]
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[ 6126-49-4 ]
| Yield | Reaction Conditions | Operation in experiment |
| 89 %Spectr. |
With palladium on carbon; hydrogen In tetrahydrofuran at 90℃; for 12h; |
|
|
With hydrogen In tetrahydrofuran at 90℃; for 24h; |
13
This example demonstrates the conversion of AMF to the saturated HMTF compound under hydrogen at high pressure. AMF (0.34 g, 2 mmol), THF (5 mL) and Pd/C (0.2 g) were charged to a high pressure reactor, which was pressurized to 1500 psi with H2. The reaction was stirred at 90° C. for 24 h. 1H and 13C NMR spectroscopy of the solution confirmed a quantitative conversion of AMF. HMTF was obtained as a major product. |
- 2
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[ 620-02-0 ]
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[ 6126-49-4 ]
| Yield | Reaction Conditions | Operation in experiment |
| 85% |
With hydrogen In water at 140℃; for 2h; Autoclave; |
2.2 General procedure for FFA hydrogenation
General procedure: In a typical run, FFA (100mg), catalyst (10mg) and water (10mL) were placed in a stainless Parr autoclave (25mL). After purging the reactor several times with H2 (99.99%). The reactions were subsequently conducted at the desired temperature and stirred at 600rpm. At the end of the reaction, the reactor was cooled to room temperature and the pressure was released and the catalyst was isolated from the solution by centrifugation, washed with i-PrOH and reused directly in the next run. The reaction solution was analyzed by GC/MS (Agilent 7890) equipped with a HP-innowax capillary column (30m×0.25mm) using the n-dodecane as an internal standard. The conversion and yield were evaluated on the basis of the amounts of furfural. The conversion of furfural (mol%) and products yield (mol%) were calculated according to the following formula: (1) Conversion=moleofreactedsubstratetotalmoleofsubstratefeed100% Conversion=moleofreactedsubstratetotalmoleofsubstratefeed100% (2) YieldofCPL=moleofCPLtotalmoleofsubstratefeed100% YieldofCPL=moleofCPLtotalmoleofsubstratefeed100% (3) Yieldofotherproducts=moleofcorrespondingproductstotalmoleofsubstratefeed100% Yieldofotherproducts=moleofcorrespondingproductstotalmoleofsubstratefeed100% |
|
With 5%-palladium/activated carbon; hydrogen at 25 - 180℃; for 6.5h; Autoclave; |
27 Example 27
In an autoclave equipped with a glass inner tube with an internal volume of 50 ml, 150 mg of 5 mass% palladium / carbon (AD type manufactured by Kawaken Fine Chemical Co., Ltd.), 1.50 g (13.6 mmol) of 5-methylfurfural, 50 g was added and pressurized to 8 MPa with hydrogen (12 mol with respect to 1 mol of 5-methylfurfural), followed by heating at 25 ° C. for 2.5 hours, at 55 ° C. for 2.5 hours and further at 180 ° C. 3 For 2 hours. After completion of the reaction, the obtained reaction solution was cooled to 25 ° C., and then filtered with a syringe equipped with a membrane filter (0.45 μm). --°C°C°C °Cμ [0082] Submit CorrectionsCloseAnalysis of the obtained filtrate by gas chromatography revealed that the conversion of 5-methylfurfural was 100 mol%, the yield of 2-hydroxymethyl-5-methyltetrahydrofuran was 95.7 mol%, the selectivity Was 95.7 mol% |
|
With hydrogen |
|
Reference：
[1]Xia, Haihong; Li, Jing; Chen, Changzhou; Wu, Dichao; Ren, Jurong; Jiang, Jianchun; Zhou, Minghao
[Inorganic Chemistry Communications, 2021, vol. 133]
[2]Current Patent Assignee: UBE INDUSTRIES LIMITED - JP6168044, 2017, B2
Location in patent: Paragraph 0079; 0080; 0081
[3]Chen, Kaiyou; Mori, Kazuma; Nakagawa, Yoshinao; Tomishige, Keiichi; Watanabe, Hideo
[Journal of Catalysis, 2012, vol. 294, p. 171 - 183,13]
- 3
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[ 10551-58-3 ]
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[ 96-47-9 ]
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[ 1003-38-9 ]
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[ 6126-49-4 ]
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2-(acetoxymethyl)-5-cyclohexyl-2-methyltetrahydrofuran
[ No CAS ]
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(5-(hydroxymethyl)tetrahydrofuran-2-yl)methyl acetate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
With palladium 10% on activated carbon; hydrogen In ethyl acetate for 2h; |
35
Using the same apparatus and standard conditions as used in examples 1 - 32, a series of experiments was performed using a solution of AcMF furan starting material in solvent and catalyst systems. These studies were conducted to determine the effect of varying catalyst systems, reaction times and pressures, on AcMF conversion and furan derivative selectivity. An EtOAc solution of AcMF in the presence of a catalyst system was pressurized to 60 bar hydrogen and heated for 1 h. Results indicate the catalyst system comprising a combination of Pd/C and acid promoter trifluoracetic acid (Table 4, entry 33) gave a mixture of 46% fully reduced furan derivative (7b), 26% of 4b, 16% MTHF (15), and 5% DMTHF (6). The selectivity of DMTHF under the same conditions using the multifunctional catalyst system, Amberlyst 28, gave 48% higher selectivity as compared to the combined catalyst system. Increasing the reaction time to 2 h provided even higher selectivity of DMTHF at 63%. The multifunctional catalyst system of Amberlyst 10 at 14 bar hydrogen pressure, with heating to 60°C for 1 h, gave a 25% selectivity of the furan derivative MTHF, and partial conversion of AcMF. The results demonstrate the selectivity of furan derivatives was controlled by the choice of catalyst system, reaction temperature, and reaction time. Table 4. Furan derivative selectivity from AcMF using a combination of catalyst and acid promoter and multifunctional catalyst systems. |
|
With palladium 10% on activated carbon; hydrogen; trifluoroacetic acid In ethyl acetate at 60℃; for 1h; |
36
Using the same apparatus and standard conditions as used in examples 1 - 32, a series of experiments was performed using a solution of AcMF furan starting material in solvent and catalyst systems. These studies were conducted to determine the effect of varying catalyst systems, reaction times and pressures, on AcMF conversion and furan derivative selectivity. An EtOAc solution of AcMF in the presence of a catalyst system was pressurized to 60 bar hydrogen and heated for 1 h. Results indicate the catalyst system comprising a combination of Pd/C and acid promoter trifluoracetic acid (Table 4, entry 33) gave a mixture of 46% fully reduced furan derivative (7b), 26% of 4b, 16% MTHF (15), and 5% DMTHF (6). The selectivity of DMTHF under the same conditions using the multifunctional catalyst system, Amberlyst 28, gave 48% higher selectivity as compared to the combined catalyst system. Increasing the reaction time to 2 h provided even higher selectivity of DMTHF at 63%. The multifunctional catalyst system of Amberlyst 10 at 14 bar hydrogen pressure, with heating to 60°C for 1 h, gave a 25% selectivity of the furan derivative MTHF, and partial conversion of AcMF. The results demonstrate the selectivity of furan derivatives was controlled by the choice of catalyst system, reaction temperature, and reaction time. Table 4. Furan derivative selectivity from AcMF using a combination of catalyst and acid promoter and multifunctional catalyst systems. |
- 4
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[ 10551-58-3 ]
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[ 1003-38-9 ]
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[ 6126-49-4 ]
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2-(acetoxymethyl)-5-cyclohexyl-2-methyltetrahydrofuran
[ No CAS ]
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(5-(hydroxymethyl)tetrahydrofuran-2-yl)methyl acetate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
With palladium 10% on activated carbon; hydrogen; trifluoroacetic acid In ethyl acetate for 1h; |
Using the same apparatus and standard conditions as used in examples 1 - 32, a series of experiments was performed using a solution of AcMF furan starting material in solvent and catalyst systems. These studies were conducted to determine the effect of varying catalyst systems, reaction times and pressures, on AcMF conversion and furan derivative selectivity. An EtOAc solution of AcMF in the presence of a catalyst system was pressurized to 60 bar hydrogen and heated for 1 h. Results indicate the catalyst system comprising a combination of Pd/C and acid promoter trifluoracetic acid (Table 4, entry 33) gave a mixture of 46% fully reduced furan derivative (7b), 26% of 4b, 16% MTHF (15), and 5% DMTHF (6). The selectivity of DMTHF under the same conditions using the multifunctional catalyst system, Amberlyst 28, gave 48% higher selectivity as compared to the combined catalyst system. Increasing the reaction time to 2 h provided even higher selectivity of DMTHF at 63%. The multifunctional catalyst system of Amberlyst 10 at 14 bar hydrogen pressure, with heating to 60°C for 1 h, gave a 25% selectivity of the furan derivative MTHF, and partial conversion of AcMF. The results demonstrate the selectivity of furan derivatives was controlled by the choice of catalyst system, reaction temperature, and reaction time. Table 4. Furan derivative selectivity from AcMF using a combination of catalyst and acid promoter and multifunctional catalyst systems. |
- 5
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[ 10299-30-6 ]
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[ 89791-47-9 ]
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[ 6126-49-4 ]
| Yield | Reaction Conditions | Operation in experiment |
| 1: 7.42 %Chromat.
2: 75.47 %Chromat. |
With bismuth(lll) trifluoromethanesulfonate at 130℃; for 2h; |
18 Example 18
Example 18 Preparation of 5-methyltetrahydrofuran-2-methanol from 1,2,5 hexanetriol A mixture of 817 milligrams 1,2,5 hexanetriol and 40 milligrams of bismuth triflate was reacted under vacuum (200 torr) at 130° C. for 2 hours. The resulting residue was cooled to room temperature. A sample analyzed by gas chromatography indicated that the starling hexane-1,2,5-triol was completely converted and that the residue contained 75.47% (by weight) of the desired methyltetrahydrofuran-2-methanol. Also produced at a 7.42% weight yield was the isomer 2-methyl-4-tetrahydropyranol. |
- 6
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1,6-anhydro-3,4-dideoxy-β-D-threo/erythro-hexopyranose
[ No CAS ]
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[ 6126-49-4 ]
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[ 2144-40-3 ]
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[ 81370-88-9 ]
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(6S)-6-(hydroxymethyl)dihydro-2H-pyran-3(4H)-one
[ No CAS ]
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tetrahydropyran-2-methanol-5-hydroxyl
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 1: 42.5 %Chromat.
2: 15.4 %Chromat.
3: 17.1 %Chromat.
4: 20.1 %Chromat.
5: 3.4 %Chromat. |
With hydrogen In tetrahydrofuran at 150℃; for 3h; |
|
- 7
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[ 67-47-0 ]
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[ 7326-46-7 ]
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[ 6126-49-4 ]
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[ 100-72-1 ]
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[ 2144-40-3 ]
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[ 110-13-4 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With palladium on activated charcoal; water; hydrogen at 170℃; for 2h; Autoclave; |
|
- 8
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[ 67-56-1 ]
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[ 67-47-0 ]
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[ 97-99-4 ]
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[ 6126-49-4 ]
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[ 100-72-1 ]
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[ 2144-40-3 ]
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[ 106-69-4 ]
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[ 107-31-3 ]
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trans-tetrahydro-(5-(methoxymethyl)furan-2-yl)methanol
[ No CAS ]
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cis-tetrahydro-(5-(methoxymethyl)furan-2-yl)methanol
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
With palladium on activated charcoal; hydrogen at 170℃; for 2h; Autoclave; |
|
- 9
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[ 67-47-0 ]
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[ 6126-49-4 ]
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[ 1883-75-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With 5 wt% ruthenium/carbon; hydrogen In water at 100℃; for 0.5h; Autoclave; |
2.2 Hydrogenation of HMF
General procedure: Hydrogenation reactions were carried out in a 300mL stainless steel Parr 4560 autoclave equipped with a P.I.D. controller (4843). In a typical experiment, a weight ratio metal to HMF of 1wt% was used. In this regard, the catalyst employed as received, was weighted and introduced into the autoclave, which was subsequently closed and evacuated to 65Pa with a mechanical vacuum pump. 50mL of a HMF aqueous solution was introduced into the autoclave by suction, and the reaction mixture was stirred using a mechanical overhead stirrer. Then, the reactor was pressurized with hydrogen till the desired pressure was reached at the pre-set temperature, always under mechanical stirring. The pressure in the reactor was manually held constant at the pre-determined value by repeated hydrogen addition, when necessary. The reaction progress was monitored by sampling periodically the liquid through a dip tube. The liquid samples were analysed using HPLC. All the experiments were carried out in triplicate and the reproducibility of the techniques was within 3%. For the recycling tests, the employed catalyst was recovered by filtration and re-used within two subsequent runs. At the end of the third cycle, the recovered catalyst was washed with acetone, dried and re-used for an additional recycling test. |
Reference：
[1]Fulignati, Sara; Antonetti, Claudia; Licursi, Domenico; Pieraccioni, Matteo; Wilbers, Erwin; Heeres, Hero Jan; Raspolli Galletti, Anna Maria
[Applied Catalysis A: General, 2019, vol. 578, p. 122 - 133]
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