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Synonyms: γ-Valerolactone; γ-VL; NSC 33700, γ-Valerolactone, γ-VL
4.5
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CAS No. : | 108-29-2 |
Formula : | C5H8O2 |
M.W : | 100.12 |
SMILES Code : | O=C1OC(C)CC1 |
Synonyms : |
γ-Valerolactone; γ-VL; NSC 33700, γ-Valerolactone, γ-VL
|
MDL No. : | MFCD00005400 |
InChI Key : | GAEKPEKOJKCEMS-UHFFFAOYSA-N |
Pubchem ID : | 7921 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
Example 5; Synthesis of acetic acid 3-[1-acetyl-5-chloro-2-(4-methoxy-phenyl)-1H-indol-3-yl]-1-methyl-propyl ester; Step A: To a solution of N-(4-chloro-phenyl)-2,2-dimethyl-propionamide (14.2 mmol, 3 g) in dry THF (15 ml) under argon atmosphere 22 ml of a 1.6 M solution of n-butyl lithium in hexanes was added at -50 C. The reaction mixture was stood for 2 hours at 0 C. during which time a white precipitate formed. The mixture was cooled to -40 C. and solution of gamma-valerolactone (17 mmol, 1.6 ml) in 10 ml of dry THF was added dropwise. After stirring for 1 hour at this temperature, the reaction mixture was quenched with saturated aqueous solution of ammonium chloride. The mixture was extracted with dichloromethane (2×50 ml), the organic layer was dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The crude residue was used for the next step without further purification. The residue was dissolved in dioxane and 80 ml of 3 N HCl was added. The solution was refluxed for 12 hours. After cooling to room temperature, the solution was neutralized with 1 N solution of sodium hydroxide followed by extraction with DCM. The organic layer was dried over anhydrous sodium sulfate, evaporated to yield a crude product. Purification was performed on silica gel (ethyl acetate:hexanes) to obtain 1-(2-amino-5-chloro-phenyl)-4-hydroxy-pentan-1-one as a yellow solid in moderate yield (0.96 g, 29% yield). 1H NMR (250 MHz, CDCl3): delta7.73 (d, J=2.4 Hz, 1H), 7.18 (dd, J=8.8 Hz, 1H), 6.60 (d, J=8.7 Hz, 1H), 6.25 (broad s, 2H), 3.92-3.81 (m, 1H), 3.10-3.04 (m, 2H), 1.89-1.81 (m, 2H), 1.24 (d, J=6.2 Hz, 3H). 13C NMR (250 MHz, CDCl3): delta202.0, 148.8, 134.3, 130.3, 120.0, 118.8, 67.5, 35.5, 33.3, 23.8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen; at 199.84℃; under 30003.0 Torr; for 4h;Autoclave;Catalytic behavior; | In a typical reaction, the batch autoclave reactor was loaded with catalyst, substrate, and solvent, purged three times with argon after which the reaction mixture was heated to reaction temperature and charged with H2 to 40 bar. This was taken as the starting point of the reaction. After the reaction was cooled to room temperature, the H2 was released, and 2 wtpercent anisole was added as internal standard. The catalyst was separated by centrifugation, filtration, and finally washed with acetone. The reaction products were analyzed using a Shimadzu GC-2010A gas chromatograph equipped with a CP-WAX 57-CB column (25 m × 0.2 mm × 0.2 mum) and FID detector. Products were identified with a GC?MS from Shimadzu with a CP-WAX 57CB column (30 m × 0.2 mm × 0.2 mum). The gas-phase reaction products were analyzed by an online dual channel Varian CP4900 micro-GC equipped with a COX column and TCD detector, for analysis of H2, CO2, CO, and CH4. Dioxane runs were performed with 10 wtpercent levulinic acid (2.5 g, 21.5 mmol) in dioxane (22.5 g) over a series of 1 wtpercent Ru catalysts (0.3 g) containing different supports. The reactions were run in a 50 mL Parr batch autoclave at a temperature of 473 K for 4 h using a hydrogen pressure 40 bar and a stirring speed of 1600 rpm. 2-Ethylhexanoic acid runs were performed with 10 wtpercent levulinic acid (6.0 g, 51.7 mmol) in 2-ethylhexanoic acid (54 g) with 1 wtpercent Ru catalysts (0.6 g). The reactions were run in 100 mL Parr batch autoclave at a temperature of 473 K for 10 h using a hydrogen pressure 40 bar and a stirring speed of 1600 rpm. 1 mL of solution was sampled at various intervals during the reaction. Reactions with intermediates GVL (2.2 g, 21.5 mmol) or PEA (2.2 g, 21.5 mmol) in EHA (22.8 g) were conducted with 0.3 g of catalyst in the 50 mL Parr batch autoclave. Finally, neat LA runs were performed with LA (20 g, 172 mmol) over 1 wtpercent Ru catalysts (0.3 g or 0.5 g). The reactions were run in a 50 mL Parr batch autoclave at a temperature of 473 K for 4 h and 10 h using a hydrogen pressure 40 bar and a stirring speed of 1600 rpm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16.8% | With graphene oxide-supported zirconia; at 180℃; under 7500.75 Torr; for 3h;Inert atmosphere; Sealed tube; Autoclave; | General procedure: The transfer hydrogenation of ethyl levulinate into GVLwas performed in a stainless steel 40 mL Parr batch reactor.A representative procedure was as follows: ethyl levulinate(1 mmol), ZrO2/GO (40 mg) catalyst and iso-propanol(10 mL) were charged in the reactor. The air in the reactorwas exchanged with nitrogen for five times and sealed underN2pressure (1.0 MPa). Then the autoclave was heated fromroom temperature to 180 C within 10 min and then the reactionwas performed at 180 C for 3 h. After cooling the reactorto room temperature, the reaction mixture was filtrated,and the clear solution was analyzed by gas chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ruthenium supported on montmorillonite K10; at 120℃; under 30003 Torr;Autoclave; | General procedure: 160ml, Parr). Autoclave was flled with an appropriateamount of catalyst (10wt% in case of Ru catalysts, 20wt%in case of Ni catalysts, based on levulinic acid), levulinicacid (10g, Merck, 98%), internal standard-mesitylene(0.8g, Acros Organics, 99%) and 100ml of solvent-toluene,1,4-dioxane, heptane, cyclohexane, methanol, propan-2-ol, propan-1-ol, butan-1-ol, ethyl acetate (all Penta, p.a.),ethanol (Penta, 96.5%) or butan-2-ol (Lachema, 99%). Samplestaken during the reaction were centrifuged and analyzedusing gas chromatograph coupled with mass detector(Shimadzu 2010 Plus, GCMS-QP2010 Ultra) equipped withnonpolar column DB-5. Injector temperature was 250C,the programmed temperature program ranged from 80C to250C using rate 10Cmin-1, detector voltage was 0.8kVand ion source had temperature 220C. Experiments wererepeated two times and the error between these two measurementswas not higher than 8%. Reuse experiment: reactionmixture was centrifuged, catalyst was separated and washed3 times with toluene (10ml). Wet catalyst was mixed withfresh reactants and the reaction was performed as usual. |
Tags: gamma-Valerolactone | γ-Valerolactone | Tetrahydrofurans | Ketones | Furans | Organic Building Blocks | Heterocyclic Building Blocks | 108-29-2
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