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CAS No. : | 106-02-5 | MDL No. : | MFCD00039667 |
Formula : | C15H28O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FKUPPRZPSYCDRS-UHFFFAOYSA-N |
M.W : | 240.38 | Pubchem ID : | 235414 |
Synonyms : |
15-Pentadecanolactone
|
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 |
---|---|---|
91% | at 60℃; for 16 h; Autoclave; Inert atmosphere | Example B-2 Preparation of 15-bromopentadecanoic acid 15-Pentadecanolide of 14.3 g (59.5 mmol), and 32percent hydrogen bromide/acetic acid solution of 24.8 g (98.0 mmol, 1.6 eq) were added to 100 mL of autoclave protected with Teflon (registered trade name). After purging with nitrogen and sealing, the autoclave was placed in an oil bath at 60°C and stirring was carried out for 16 hours. For the stirring, a magnetic stirrer was used. After cooling, 14 mL of water was added, and by using 200 mL of hot hexane the mixture was transferred to a separatory funnel. After washing with ion exchange water, it was dried over the magnesium sulfate. After filtration, 17.4 g of the target compound was obtained by crystallization using n-hexane (yield 91percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47 %Chromat. | at 60 - 100℃; for 46 h; Inert atmosphere | Example B-3 Preparation of 15-bromopentadecanoic acid (open system) To a two-necked 50 mL of flask equipped with a refluxing condenser tube and a magnetic stirrer, 15-pentadecanolide of 1. 0 g (4.2 mmol), and 32percent hydrogen bromide/acetic acid solution of 3.3g (13.1 mmol, 3.1 eq) were added. The flask was placed in an oil bath at 60°C and stirring was carried out for 16 hours under nitrogen atmosphere. Sampling analysis based on GC indicated that area percentage consisted of the target compound 15-bromopentadecanoic acid 10percent, the starting material 15-pentadecanolide 89percent and byproduct 15-acetoxypentadecanoic acid 1percent. Further, after heating and stirring in an oil bath at 80°C for 8 hours, the area percentage consisted of the target compound 31percent, the starting material 65percent and byproduct 4percent. Further, after heating and stirring in an oil bath at 100°C for 20 hours, the area percentage consisted of the target compound 42percent, the starting material 52percent, and by product 6percent. Still further, after 32percent hydrogen bromide/acetic acid solution 3 g (11.9 mmol, 2.8 eq) were added and then the resultant was heated and stirred in an oil bath at 100°C for 2 hours, the area percentage consisted of the target compound 47percent, the starting material 47percent, and byproduct 6percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.6% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 72h; | Pentadecanolide (5 g, 20.8 mmol) dissolved in tetrahydrofuran (150 mL) was cooled to 0C, and to the resultant solution, aluminum lithium hydride (1.2 g, 31.2 mmol) was added in portions. The temperature of the mixture was then returned to room temperature. The reaction mixture was stirred for three days at room temperature, and subsequently, an aqueous saturated tartaric acid solution (200 mL) was added thereto at 0C. The mixture was subjected to extraction with ethyl ether three times. The organic layers were combined, washed with aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure, to thereby yield 5.01 g (20.5 mmol) of 1,15-pentadecanediol. Yield: 98. 6% Rf (hexane/ethyl acetate = 10/90) = 0. 44 |
97% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 4h;Inert atmosphere; | Lithium aluminiumhydride (3.42 g, 90 mmol, 1.8 eq) was suspended in dry THF (120 mL) and cooled to 0 C. Then a solution of 15-pentadecanolide (12 g, 50 mmol, 1 eq) in THF (80 mL) was added drop wise. The solution was stirred for 1 h at 0 C and then at r.t. for 3 h. The reaction was quenched with aq. sodium potassium tartrate solution (20 mL), the organic layer was separated and aqueous layer was extracted with EtOAc (2 100 mL). The combined organic layer was dried over MgSO4 and evaporated to get colourless solid. Yield: 11.9 g (97%). M.p.: 89 C. 1H NMR (300 MHz, DMSO-d6): delta = 1.19 - 1.31 (m, 18H, 4-CH2 to 12-CH2), 1.39 (quin, 3JH,H = 6.7 Hz, 8H, 2-CH2, 3-CH2, 13-CH2, 14-CH2), 4.33 (t, 3JH,H = 5.2 Hz, 4H, 1-CH2, 15-CH2) ppm. 13C NMR (75 MHz, DMSO-d6): delta = 25.4 (C-3, C-13), 28.9 (C-5, C-11), 29.0 (C-6 to C-10), 29.06 (C-4, C-12), 32.4 (C-2, C-14), 60.6 (C-1, C-15) ppm. HRMS (ESI+): m/z C15H32O2 + H+: calcd. 245.2481, found 245.2475; C15H32O2 + Na+: calcd. 267.2300, found 267.2295. |
96% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 4h;Inert atmosphere; | Lithium aluminium hydride (1.52 g, 40.0 mmol, 2.0 eq.) was suspended in dry THF (80 mL) under an argon atmosphere. A solution of 15-pentadecanolide (4.80 g, 20.0 mmol) in dry THF (200 mL) was added at 0 C. Stirring was continued at this temperature for 1 h and for 3 more hours at r.t.. Potassium sodium tartrate solution (20%, 50 mL) was added dropwise to the stirred reaction mixture. The phases were separated and the aqueous phase was extracted with diethyl ether (3 chi 100 ml). The combined organic layers were dried over MgS04. The solvent was removed in vacuo and the product was isolated as a white solid, which was used for the next step without purification. Yield: 4.68 g (96%). 22 M.p.: 86-87 C (lit. 87 C) 1H-NMR (300 MHz, CDCI3) delta [ppm]: 1.28-1 .33 (m, 24 H, 3-CH2 to 13-CH2, 1 -OH, 15-OH), 1 .53 (m, 4 H, 2-CH2, 14-CH2), 3.55 (t, 3JH,H = 6.8 Hz, 4 H, 1 -CH2, 15-CH2). 13C-NMR (75 MHz, CDCI3) delta [ppm]: 26.4 (t, C-3, C-13), 30.1 , 30.3 (t, C-4 to C-12), 33.1 (t, C-2, C-14), 62.7 (t, C-1 , C-15). Refs.: Synthesis according to C. Girlanda-Junges, F. Keyling-Bilger, G. Schmitt, B. Luu, Tetrahedron 1998, 54, 7735-7748. M.p. P. Chuit, J. Hausser, Helv. Chim. Acta 1929, 12, 850-859. |
96% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 4h;Inert atmosphere; | 4.9 Pentadecane-i, i5-diol10256] Lithium aluminium hydride (1.52 g, 40.0 mmol, 2.0 eq.) was suspended in dry THF (80 mE) under an argon atmosphere. A solution of 1 5-pentadecanolide (4.80 g, 20.0 mmol) in dry THF (200 mE) was added at 0 C. Stirring was continued at this temperature for 1 h and for 3 more hours at tt. Potassium sodium tartrate solution (20%, 50 mE) was added dropwise to the stirred reaction mixture. The phases were separated and the aqueous phase was extracted with diethyl ether (3xiOO ml). The combined organic layers were dried over Mg504. The solvent was removed in vacuo and the product was isolated as a white solid, which was used for the next step without purification. Yield: 4.68 g (96%).2210257] M.p.: 86-87 C. (lit. 87 C.)10258] ?H-NMR (300 MHz, CDC13) oe [ppm]: 1.28-1.33(m, 24H, 3-CH2 to i3-CH2, i-OH, iS-OH), 1.53 (m, 4H,2-CH2, i4-CH2), 3.55 (t, 3J,y=6.8 Hz, 4H, i-CH2, i5-CH2).10259] ?3C-NMR (75 MHz, CDC13) oe [ppm]: 26.4 (t, C-3,C-i3), 30.1,30.3 (t, C-4 to C-i2), 33.1 (t, C-2, C-i4), 62.7 (t,C-i, C-is).10260] Refs.: Synthesis according to C. Girlanda-Junges, F.Keyling-Bilger, G. Schmitt, B. Euu, Tetrahedron 1998, 54,7735-7748.10261] M.p. P. Chuit, J. Hausser, Helv. Chim. Acta 1929, 12,850-859. |
95% | General procedure: Under an atmosphere of N2, a suspension of LiAlH4 (228 mg, 6.01 mmol, 11.6 equiv) in dry THF (6 mL) was stirred at rt for 5 min. The mixture was cooled to 0 C, and a solution of pentadecanolide (500 mg, 2.08 mmol, 1 equiv) in THF (6 mL) was added. The reaction mixture was brought to rt and then stirred at reflux temperature for 2 h. The mixture was cooled to 0 C and then an aqueous solution of NaOH (2 M, 2 mL) was added. A white precipitate was formed and the mixture was stirred at reflux temperature for 0.5 h. The mixture was extracted with Et2O (2 × 50 mL). The combined organic extracts were washed with brine (2 × 20 mL), dried (Na2SO4), and concentrated. High-vacuum drying gave 1,15-pentadecanediol (482 mg, 1.97 mmol, 95%) as a white solid; | |
78% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 - 25℃;Inert atmosphere; | To a stirred suspension of lithium aluminium hydride (2.8 g, 74.5 mmol) in anhydrous THF (250 mL) at 0C under an argon atmosphere was added a solution of 15-pentadecanolide (7.9 g, 33.1 mmol, 0.3M solution in anhydrous THF) in dropwise over 30 min. After being stirred for 1h at the same conditions and for additional 2h at ambient temperature (as monitored by TLC analysis, cyclohexane/EtOAc 6:4; Rf(adduct) = 0.67; Rf(product) = 0.34; visualized with Seebach reagent), the reaction was cooled again to 0C and carefully quenched with an ice-cold 10% aqueous potassium hydroxide solution (20 mL). The resulting mixture was allowed to stir for 30 min at ambient temperature, before it was filtered through a pad of Celite, which was rinsed several times with ethylacetate (3x100 mL). The combined organic filtrates were washed with brine solution (200 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford compound 1,15-pentadecanediol as white solid. The product was directly used in the next step without any further purification. Yield: 6.3 g (78%). Rf: 0.32 (cyclohexane/EtOAc 6:4, visualized with Seebach reagent). 1H-NMR (CDCl3, 500 MHz, ppm) delta 3.64 (t, J = 6.6 Hz, 4H), 1.60 - 1.53 (m, 4H), 1.38 - 1.24 (m, 20H). 13C-NMR (CDCl3, 126 MHz, ppm) delta 63.25, 32.95, 29.76, 29.73, 29.71, 29.56, 25.87. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With 2,2'-diperoxyphenic acid In 1,2-dichloro-ethane at 60℃; for 48h; Schlenk technique; | |
86% | With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 108h; | 6.aj Oxacyclohexadecan-2-one (XXX VIII) m-Chloroperoxybenzoic acid (m-CPBA, 70% pure, 687 mg, 2.79 mmol) was added to a solution of cyclopentadecanone (500 mg, 2.23 mmol) in CH2C12(6 mL) at 0 °C and the reaction stirred at rt for four days and 22 hours. 1H NMR analysis of a reaction aliquot taken after three days indicated 74% consumption of ketone and at this point an extra portion of m-CPBA (150 mg) was added. After four days and 22 hours, the reaction was diluted with CH2C12(20 mL), washed with sat. aq. NaHC03, (3 x 20 mL), water (20 mL) and brine (20 mL) and concentrated under reduced pressure to give the crude product. Silica gel chromatography (5% to 10% ethyl acetate/hexanes) gave lactone XXXVIII (463 mg, 86%) as a colourless oil.1H NMR (400 MHz, CDC13) δ 4.15 - 4.11 (m, 2H), 2.35 - 2.29 (m, 2H), 1.71 - 1.58 (m, 4H), 1.45 - 1.27 (m, 20H). |
70% | Stage #1: cyclopentadecanone With N-hydroxyphthalimide; 1,1-Diphenylmethanol; 2,2'-azobis(isobutyronitrile); oxygen In acetonitrile at 75℃; for 22h; Stage #2: With 1,1,1,3',3',3'-hexafluoro-propanol; toluene-4-sulfonic acid at 60℃; Inert atmosphere; |
With potassium peroxomonosulphate; sulfuric acid; Petroleum ether at 50 - 65℃; | ||
With 3-chloro-benzenecarboperoxoic acid In chloroform Heating; | ||
Bayer-Villiger oxidation; | ||
With boron trifluoride diethyl ether complex; 3-chloro-benzenecarboperoxoic acid 1) dichloromethane, 15 min, 2) 15 h, 40 deg C; Yield given. Multistep reaction; | ||
58 %Chromat. | Stage #1: cyclopentadecanone With 1,1-Diphenylmethanol; 2,2'-azobis(isobutyronitrile); oxygen In acetonitrile at 75℃; for 20h; Stage #2: With 1,1,1,3',3',3'-hexafluoro-propanol; toluene-4-sulfonic acid at 60℃; for 24h; | 16 EXAMPLE 16 A mixture of 6 mmol of benzhydrol, 2 mmol of cyclopentadecanone, 0.3 mmol of N-hydroxyphthalimide, 0.15 mmol of azobisisobutyronitrile (AIBN), and 3 mL of acetonitrile was stirred at 75°C in an oxygen atmosphere (at 1 atmosphere, i.e., 0.1 MPa) for 20 hours. Subsequently the solvent was removed, and 6 mL of hexafluoroisopropanol and 0.02 mmol of p-toluenesulfonic acid were added, followed by stirring at 60°C for 24 hours. The reaction mixture was analyzed by gas chromatography and found that there was produced cyclopentadecanolide in a yield of 58% on the basis of cyclopentadecanone. |
With sodium hypophosphite; nicotinamide adenine dinucleotide phosphate; monooxygenase from Thermothelomyces thermophila In 1,4-dioxane at 30℃; for 24h; Enzymatic reaction; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With p-nitrobenzoic anhydride; scandium tris(trifluoromethanesulfonate) In tetrahydrofuran; acetonitrile Heating; Yields of byproduct given; | |
1: 92% 2: 1% | With dmap; 2-methyl-6-nitrobenzoic anhydride In dichloromethane at 20℃; for 15h; | |
92% | With dmap; di-2-thienyl carbonate In toluene; acetonitrile at 100℃; for 5h; |
90% | With dmap; iodine; di-2-thienyl carbonate In toluene; acetonitrile for 10h; Heating; | |
1: 88% 2: 10% | With chloro-trimethyl-silane; TiCl2(OTf)2; 4-(trifluoromethyl)benzoic anhydride In dichloromethane Heating; | |
1: 88% 2: 3% | With dmap; 2-methyl-6-nitrobenzoic anhydride; triethylamine In dichloromethane at 20℃; | |
1: 88% 2: 5% | With chloro-trimethyl-silane; TiCl2(OTf)2; 4-(trifluoromethyl)benzoic anhydride In dichloromethane at 50℃; for 5h; | |
1: 88% 2: 5.5% | With pentafluorobenzoylchloride; triethylamine In toluene at 110℃; for 24h; | |
1: 63% 2: 8% | With di(n-butyl)tin oxide In 1,3,5-trimethyl-benzene for 23h; Heating; | |
1: 2.1% 2: 4.3% | With dealuminated HY zeolite In neat (no solvent) at 90℃; for 6h; other reagents; var. temp. and reaction times; also with perfluorotributylamine addition and 'in pore' method; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 36% 2: 22% | With toluene-4-sulfonic acid In benzene for 21h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With (Z)-9-octadecen-1-amine; lipase PS from Pseudomonas cepacia; water In Hexadecane at 40℃; for 0.5h; Miniemulsion system; Enzymatic reaction; | |
100% | With sodium hydroxide In tetrahydrofuran; methanol; water | |
99% | With potassium hydroxide In methanol; water for 5.5h; Heating; |
98% | With potassium hydroxide In ethanol for 2h; Heating; | |
97% | With water; potassium hydroxide In methanol at 80℃; for 6h; | |
97% | With tetrabutylammomium bromide; potassium hydroxide In tetrahydrofuran; water for 12h; Reflux; | 10 5.1.3.10. 15-(Benzo[d]oxazol-2-ylthio)-N-(2,6-diisopropylphenyl)-pentadecanamide (3j) 15-Pentadecanolactone (10.0 g, 42 mmol), KOH (10.0 g, 0.18 mmol) and n-Bu4NBr (1.34 g, 4.2 mmol) were dissolved ina mixed solvent of tetrahydrofuran (THF) (100 mL) and water (30 mL). The reaction mixture was heated under reflux for 12 h·THF solvent wa sevaporated under reduced pressure. The aqueous layer was made acidic (pH=l) with 10% H2SO4 solution and then extracted with Et2O. The organic layer was washed with water and brine and dried over MgSO4. After filtration, the solvent was evaporated under reduced pressure. The residue was crystallized from acetone to give 15-hydroxypentadecanoic acid (10.4 g, 97%) as colorless crystals. To a solution of the thus obtained carboxylic acid (15.2 g, 20 mmol) and 1 (5.3 g, 30 mmol) in DMF (40 mL) were added WSC (4.2 g, 22 mmol) and HOBt (3.0 g,22 mmol) at rt. The resulting mixture was stirred at rt for 12 h. Water was added to the reaction mixtures, and the formed precipitate was filtered off and extracted with CHCl3. The organic layer was washed with 1-N HCl solution and brine and dried over MgSO4. After filtration, the solvent was evaporated under reduced pressure. The residue was extracted with Et2O and the insoluble material was filtered off. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography and eluted with acetone/n-hexane (1:5) to give 15-hydroxy-N-(2,6-diisopropylphenyl)pentadecanamide (1.9 g, 23%) as a white solid. To a solution of the thus obtained alcohol (1.64 g, 3.9 mmol) in pyridine (15 mL) were added p-toluenesulfonyl chloride (TsCl) (1.65 g, 6.7 mmol) and N,N-dimethyl-4-aminopyridine (DMAP) (24 mg 0.2 mmol) at 0 °C. The resulting mixture was stirred at rt for 12 h. Water was added to the reaction mixture and extracted with Et2O. The organic layer was washed with 5% KHSO4 solution, brine, saturated NaHCO3 solution and brine, and dried over MgSO4. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography and eluted with Et2O/n-hexane (1:3) to give 15-(4-toluenesulfonyloxy)-N-(2,6-diisopropyl-phenyl)pentadecanamide (622 mg, 29%) and 15-chloro-N-(2,6-diisopropylphenyl)penta-decanamide (177 mg, 10%). To a solution of the thus obtained chloride (164mg, 0.38mmol) and 2-mercaptobenzoxazole (55mg, 0.36mmol) in DMF (2 mL) were added K2CO3 (55mg, 0.4mmol) and 18-crown-6 (10mg, 0.04mmol). The reaction mixture was stirred at 80°C for 1h, and then diluted with water and extracted with Et2O. The organic layer was washed with brine, and dried over MgSO4. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography, and eluted with acetone/n-hexane (1:15) to give a solid, which was recrystallized from Et2O/n-hexane to afford 3j (165mg, 83%) as colorless needles. |
96% | With sodium hydroxide In ethanol at 50℃; | |
78% | With sodium trimethylsilanolate In dichloromethane at 20℃; for 4h; Inert atmosphere; chemoselective reaction; | |
hydrolysis; | ||
With sodium hydroxide In methanol; water at 60℃; for 1h; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 21% 2: 55% | With 2,2'-azobis(isobutyronitrile); tertbutyltin hydride In benzene for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 20% 2: 40% | With toluene-4-sulfonic acid In water; toluene at 65℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With hydrogen bromide; acetic acid; at 60℃; for 16h;Autoclave; Inert atmosphere;Product distribution / selectivity; | Example B-2 Preparation of 15-bromopentadecanoic acid 15-Pentadecanolide of 14.3 g (59.5 mmol), and 32percent hydrogen bromide/acetic acid solution of 24.8 g (98.0 mmol, 1.6 eq) were added to 100 mL of autoclave protected with Teflon (registered trade name). After purging with nitrogen and sealing, the autoclave was placed in an oil bath at 60°C and stirring was carried out for 16 hours. For the stirring, a magnetic stirrer was used. After cooling, 14 mL of water was added, and by using 200 mL of hot hexane the mixture was transferred to a separatory funnel. After washing with ion exchange water, it was dried over the magnesium sulfate. After filtration, 17.4 g of the target compound was obtained by crystallization using n-hexane (yield 91percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: p-toluenesulfonic acid / 24 h / Heating 2.1: methanesulfonyl chloride / CHCl3 / Heating 2.2: LiBr / acetone / Heating | ||
Multi-step reaction with 2 steps 1: 88 percent / NaOMe / 3 h / 80 °C 2: 87 percent / NBS, PPh3 / dimethylformamide / 0.5 h / 55 °C | ||
Multi-step reaction with 3 steps 1: sulfuric acid / 24 h / 20 °C 2: triethylamine / dichloromethane / 1.5 h / 0 - 20 °C 3: lithium bromide / acetone / 5 h / Reflux |
Multi-step reaction with 2 steps 1.1: sodium / 3 h / 80 °C 1.2: 1.5 h / Reflux 2.1: N-Bromosuccinimide; triphenylphosphine; sodium hydrogencarbonate / dichloromethane / 1 h / 0 - 20 °C | ||
Multi-step reaction with 2 steps 1.1: sodium / 0 - 20 °C 1.2: 2 h / 80 °C 2.1: N-Bromosuccinimide; triphenylphosphine; sodium hydrogencarbonate / dichloromethane / 0 - 20 °C | ||
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: carbon tetrabromide; triphenylphosphine / dichloromethane / 2 h / 0 - 20 °C | ||
Multi-step reaction with 2 steps 1: methanol / 16 h / 20 °C / Inert atmosphere; Darkness 2: carbon tetrabromide; triphenylphosphine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere; Darkness | ||
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: triphenylphosphine; carbon tetrabromide / dichloromethane / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 90 percent / LiALH4 / tetrahydrofuran 2: 95 percent / HBr; H2SO4 | ||
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux 2: carbon tetrabromide; triphenylphosphine / dichloromethane / 21 h / 0 - 45 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: 71 percent / tetrahydrofuran / 1 h / 0 °C 2: 91 percent / potassium hydroxide / aq. ethanol / 2.5 h / Ambient temperature 3: 60 percent / pyridine / Ambient temperature 4: thionyl chloride / diethyl ether / 4 h / Ambient temperature 5: 94 percent / triethylamine / diethyl ether / 5 h / 40 °C 6: 1.) sodium hydride / 2.) tetrakis(triphenylphosphine)palladium(0) / 1.) THF, 45 deg C, 10 min; room temperature,30 min, 2.) reflux, 4 h 7: 82.5 percent / hexamethylphosphoric acid triamide / 11 h / 90 °C 8: 89 percent / disodium hydrogen phosphate, 6percent sodium amalgam / ethanol; tetrahydrofuran / 2.5 h / -20 °C 9: 99 percent / hydrogen / 5percent palladium on barium carbonate / 3 h / 1520 Torr / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With triethylamine In acetonitrile | 1 EXAMPLE 1 EXAMPLE 1 To a refluxing solution of 510 mg (2.0 mmol) of 2-chloro-1-methylpyridinium iodide in 50 ml of acetonitrile, there was added a solution of 134 mg (0.5 mmol) of 15-hydroxypentadecanoic acid and 404 mg (4.0 mmol) of triethylamine in 40 ml of acetonitrile over a period of 8 hours at a continuous and uniform rate, and the reaction mixture was refluxed for an additional 30 minutes after the addition was completed. After evaporation of the solvent, the residue was separated chromatographically on a silica gel column. 1,15-pentadecanolide was obtained in 84% yield. |
74% | With tributyl-amine In acetonitrile | 2 EXAMPLE 2 EXAMPLE 2 To a refluxing solution of 510 mg (2.0 mmol) of 2-chloro-1-methylpyridinium iodide in 50 ml of acetonitrile, there was added a solution of 134 mg (0.5 mmol) of 15-hydroxypentadecanoic acid and 740 mg (4.0 mmol) of tri-n-butylamine in 40 ml of acetonitrile over a period of 8 hours at a continuous and uniform rate, and the reaction mixture was refluxed for an additional 30 minutes after the addition was completed. After evaporation of the solvent, the residue was separated chromatographically on a silica gel column. 1,15-pentadecanolide was obtained in 74% yield. |
63%. | With triethylamine In toluene | 3 EXAMPLE 3 EXAMPLE 3 To a refluxing solution of 510 mg (2.0 mmol) of 2-chloro-1-methylpyridinium iodide in 50 ml of toluene, there was added a solution of 134 mg (0.5 mmol) of 15-hydroxypentadecanoic acid and 404 mg (4.0 mmol) of triethylamine in 40 ml of toluene over a period of 8 hours at a continuous and uniform rate and the reaction mixture was refluxed for and additonal 30 minutes after the addition was completed. After evaporation of the solvent, the residue was separated chromatographically on a silica gel column. 1,15 -pentadecanolide was obtained in 63%. yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With triethylamine In acetonitrile | 4 EXAMPLE 4 EXAMPLE 4 To a refluxing solution of 460 mg (2.0 mmol) of 2-chloro-1-ethylpyridinium tetrafluoroborate in 50 ml of acetonitrile, there was added a solution of 134 mg (0.5 mmol) of 15-hydroxypentadecanoic acid and 404 mg (4.0 mmol) of triethylamine in 40 ml of acetonitrile over a period of 8 hours at a continuous and uniform rate, and the reaction mixture was refluxed for an additional 30 minutes after the addition was completed. After evaporation of the solvent, the residue was separated chromatographically on a silica gel column. 1,15-pentadecanolide was obtained in 75% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With triethylamine In acetonitrile | 8 EXAMPLE 8 EXAMPLE 8 To a refluxing solution of 486 mg (2.0 mmol) of 2-chloro-1-ethyl-3-methylpyridinium tetrafluoroborate in 50 ml of acetonitrile, there was added a solution of 129 mg (0.5 mmol) of 15-hydroxypentadecanoic acid and 404 mg (4.0 mmol) of triethylamine in 40 ml of acetonitrile over a period of 8 hours at a continuous and uniform rate, and the reaction mixture was refluxed for an additional 30 minutes after the addition was completed. After evaporation of the solvent, the residue was separated chromatographically on a silica gel column. 1,15-pentadecanolide was obtained in 78% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 52 %Chromat. 2: 94 %Chromat. | Stage #1: 1,1-Diphenylmethanol; cyclopentadecanone With 2,2'-azobis(isobutyronitrile); oxygen In acetonitrile at 75℃; for 22h; Stage #2: With 1,1,1,3',3',3'-hexafluoro-propanol; toluene-4-sulfonic acid at 60℃; for 24h; | 19 EXAMPLE 19 A mixture of 6 mmol of benzhydrol, 2 mmol of cyclopentadecanone, 0.3 mmol of N-hydroxyphthalimide, 0.15 mmol of azobisisobutyronitrile (AIBN), and 3 mL of acetonitrile was stirred at 75°C in an oxygen atmosphere (at 1 atmosphere, i.e., 0.1 MPa) for 22 hours. Subsequently the solvent was removed, and 6 mL of hexafluoroisopropanol and 0.02 mmol of p-toluenesulfonic acid were added, followed by stirring at 60°C for 24 hours. The reaction mixture was analyzed by gas chromatography and found that there were produced cyclopentadecanolide in a yield of 52% on the basis of cyclopentadecanone, and diphenyl ketone in a yield of 94% on the basis of benzhydrol. The conversions from cyclopentadecanone and from benzhydrol were 91% and 99%, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47%Chromat.; 6%Chromat. | With hydrogen bromide; at 60 - 100℃; for 46h;Inert atmosphere;Product distribution / selectivity; | Example B-3 Preparation of 15-bromopentadecanoic acid (open system) To a two-necked 50 mL of flask equipped with a refluxing condenser tube and a magnetic stirrer, 15-pentadecanolide of 1. 0 g (4.2 mmol), and 32percent hydrogen bromide/acetic acid solution of 3.3g (13.1 mmol, 3.1 eq) were added. The flask was placed in an oil bath at 60°C and stirring was carried out for 16 hours under nitrogen atmosphere. Sampling analysis based on GC indicated that area percentage consisted of the target compound 15-bromopentadecanoic acid 10percent, the starting material 15-pentadecanolide 89percent and byproduct 15-acetoxypentadecanoic acid 1percent. Further, after heating and stirring in an oil bath at 80°C for 8 hours, the area percentage consisted of the target compound 31percent, the starting material 65percent and byproduct 4percent. Further, after heating and stirring in an oil bath at 100°C for 20 hours, the area percentage consisted of the target compound 42percent, the starting material 52percent, and by product 6percent. Still further, after 32percent hydrogen bromide/acetic acid solution 3 g (11.9 mmol, 2.8 eq) were added and then the resultant was heated and stirred in an oil bath at 100°C for 2 hours, the area percentage consisted of the target compound 47percent, the starting material 47percent, and byproduct 6percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 56% 2: 40% | With dmap; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In chloroform for 18h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | Stage #1: pentadecanolide With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: With hydrogen bromide In cyclohexane Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With palladium 10% on activated carbon; W(OTf)<SUB>6</SUB>; hydrogen at 135℃; for 12h; | 31 Preparation of N-Pentadecanoic acid by Pentadecanolide General procedure: Specific methods are as follows: propiolactone was added (0.36g, 5mmol), palladium on carbon (10%, 26.5mg, 0.025mmol, 0.5mol%) in the reactor and W (OTf)6(107.8mg, 0.1mmol, 2mol%). A hydrogen balloon connected to the top of the reactor, and the reactor was purged with hydrogen gas atmosphere. Hydrogen atmosphere at normal pressure, the reaction was stirred at 135 deg.] C after 12h, detected by gas, γ- valerolactone complete conversion of starting material, and only n-valeric acid. The method carried out as follows completion of the hydrogenation reaction of the ring-opening reaction system separation, to obtain the desired product n-valeric acid: The reaction was completed reaction mixture was dissolved with methylene chloride, filtered to remove the palladium on carbon catalyst and W (OTf)699% yield measured propionic acid, purity of the product was 99%. NMR data for the product using the embodiment of the present invention is the NMR identified the product as follows:The specific reaction procedure and the operation method were the same as in Example 27, and the yield was 71%, and the purity of the product was 99%. The product was subjected to nuclear magnetic identification using the manner described in the present invention, and the NMR data of the product were as follows: |
71% | With palladium on activated carbon; W(OTf)<SUB>6</SUB>; hydrogen In neat (no solvent) at 135℃; for 12h; |
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
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 |
Sorry,this product has been discontinued.
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