* 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.
Reference:
[1] Angewandte Chemie - International Edition, 2004, vol. 43, # 45, p. 6180 - 6182
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Reference:
[1] Organic Letters, 2006, vol. 8, # 7, p. 1383 - 1386
[2] Chemistry - A European Journal, 2012, vol. 18, # 30, p. 9415 - 9422
[3] Tetrahedron Letters, 1991, vol. 32, # 36, p. 4733 - 4736
[4] Journal of the American Chemical Society, 1997, vol. 119, # 23, p. 5465 - 5466
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Yield
Reaction Conditions
Operation in experiment
78%
at 90℃; for 0.5 h; Microwave irradiation
General procedure: A 10 mL reaction vessel was charged in air with Pd(PPh3)4 (6 mg, 1 mol percent), aldehyde (0.5 mmol), K2CO3 (207 mg, 1.5 mmol), benzyl chloride (70 μL, 0.6 mmol) and EtOH (1 mL). The vessel was sealed and submitted to microwave irradiation for 30 min at 90 °C, using an initial power of 30 W. (Microwave reactions were carried out with a CEM Discover 300 W monomode microwave instrument. The closed vessels used were special glass tubes with self-sealing septa that controlled pressure with appropriate sensors on the top (outside the vial). The temperature was monitored through a non-contact infrared sensor centrally located beneath the cavity floor.) The mixture was then allowed to cool to room temperature, filtered over a pad of Celite.(R). and rinsed with EtOH (5 mL). The filtrate was concentrated in vacuo and the product was purified by flash chromatography on silica gel (CH2Cl2/hexane).
With methanesulfonic acid; bis(acetylacetonato)palladium(II); 1,2-bis[di(t-butyl)phosphinomethyl]benzene In ethanol at 100℃; for 20 h; Autoclave; Inert atmosphere
A 100 ml stainless steel autoclave is charged with 19.3 mmol of 1-octene (3 ml), Pd(acac)2, 0.16 mol percent (9.4 mg), 124 tmol of BuPoX (49 mg), 10 ml of ethyl formate, 10 ml of ethanol and 28 j±1 of methanesulphonic acid under a protective gas (argon or nitrogen for example). The autoclave is heated to 120° C., followed by stirring at that temperature for 20 h. The autoclave is subsequently cooled down to room temperature and the residual pressure is released. A 5 ml quantity of isooctane is added to the reaction solution as an internal standard and the mixture is analysed by gas chromatography. The yield of n-product, i.e. ethyl nonanoate, is 94.1percent. The yield of branched products (ethyl 2-methyloc- tanoate, ethyl 2-ethylheptanoate and ethyl 2-propylhex- anoate) is altogether 4.9percent. The total yield of ethyl esters is accordingly 99percent with an n:iso ratio of 95:5.
Reference:
[1] Journal of the American Chemical Society, 1947, vol. 69, p. 1108
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Reference:
[1] Chinese Journal of Chemistry, 2011, vol. 29, # 10, p. 2153 - 2156
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Reference:
[1] Green Chemistry, 2018, vol. 20, # 15, p. 3450 - 3456
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[ 51029-20-0 ]
Reference:
[1] Journal of Chemical Research, Miniprint, 1989, # 6, p. 1264 - 1273
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Reference:
[1] Helvetica Chimica Acta, 1944, vol. 27, p. 957
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Reference:
[1] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1905, vol. <5>14, p. I,467[2] Gazzetta Chimica Italiana, 1906, vol. 36 I, p. 108
With aluminum (III) chloride; bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; at 100℃; under 19001.3 Torr; for 5h;Autoclave;
General procedure: A mixtureof 6.637 g (7.89×10-2 mol) of hexene-1, 2.289 g (4.97×10-2 mol) of ethanol, 0.080 g (11.42×10-5 mol) of PdCl2(PPh3)2, 0.180 g (6.85×10-4 mol) of PPh3, and 0.122 g (9.14×10-4 mol) of AlCl3 was charged into a 100 mL stainless steel reactor equipped with a stirrer and a carbon(II) oxide injecting device. The pressure reactor was sealed, deaerated by flushing with carbon(II) oxide for three times, and filled with carbon(II) oxide to a pressure of 10 at; then stirring and heating were switched on. The temperature was increased to 100C during 1 h, the pressure was up to 25 at, and the reaction mixture was stirred under those conditions during 5 h. Then the vessel was cooled down to ambient, and the reaction mixture was separated by fractionation. Yield 7.0 g (84.6%) of a mixture of ethyl enanthoate and ethyl 2-methylcapronate (77.8 : 22.2).
EXAMPLE 2 A solution of 187 g of ethoxycarbonylprop-1-en-3-ylidenetriphenylphosphorane, 95 g of isopropylidenearabinose and 2 g of benzoic acid in one liter of dioxane isstirred at 60 to 70 C. for 3 hours. The residue obtained after removing the solvent in vacuo contains a mixture of cis and trans isomers of ethyl-6,9-dihydroxy-7,8-isopropylidenedioxynona-2,4-dienoate ina yield which corresponds to 62.8% of theory. The product can be hydrogenated to give the desired ethyl nonanoate as described in Example 1.
c. Additional stabilizing ligand, such as triphenylphosphine, is added to the recovered solid catalyst from step (b) in the proportion of 1 to 10 moles of ligand per mole of palladium.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; benzyl chloride; at 90℃; for 0.5h;Microwave irradiation;
General procedure: A 10 mL reaction vessel was charged in air with Pd(PPh3)4 (6 mg, 1 mol %), aldehyde (0.5 mmol), K2CO3 (207 mg, 1.5 mmol), benzyl chloride (70 muL, 0.6 mmol) and EtOH (1 mL). The vessel was sealed and submitted to microwave irradiation for 30 min at 90 C, using an initial power of 30 W. (Microwave reactions were carried out with a CEM Discover 300 W monomode microwave instrument. The closed vessels used were special glass tubes with self-sealing septa that controlled pressure with appropriate sensors on the top (outside the vial). The temperature was monitored through a non-contact infrared sensor centrally located beneath the cavity floor.) The mixture was then allowed to cool to room temperature, filtered over a pad of Celite and rinsed with EtOH (5 mL). The filtrate was concentrated in vacuo and the product was purified by flash chromatography on silica gel (CH2Cl2/hexane).