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[ CAS No. 94-50-8 ]

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2D
Chemical Structure| 94-50-8
Chemical Structure| 94-50-8
Structure of 94-50-8 *Storage: {[proInfo.prStorage]}

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Product Details of [ 94-50-8 ]

CAS No. :94-50-8MDL No. :MFCD00995104
Formula : C15H22O2 Boiling Point : 320.7°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :234.33Pubchem ID :66751
Synonyms :

Computed Properties of [ 94-50-8 ]

TPSA : 26.3 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.53 Rotatable Bond Count : 9

Safety of [ 94-50-8 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 94-50-8 ]

  • Downstream synthetic route of [ 94-50-8 ]

[ 94-50-8 ] Synthesis Path-Downstream   1~8

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YieldReaction ConditionsOperation in experiment
71% With triethylamine; In dichloromethane; at 20℃; 1.5 mmol of benzoyl chloride were dissolved in 15 mL of CH2Cl2 in around bottom flask. To this solution, 1 mmol of 1-octanol and 1.5 mmolof trimethylamine (TEA) were added. The reaction was carried out atroom temperature overnight and the solution was washed with3×15 mL of aqueous NaHCO3 and 2×15 mL of brine. The crudeproduct was purified by flash column chromatography in silica gel,using hexane:AcOEt (3:1) as eluent. 2.2.1. Octyl benzoate (1)Colorless oil; yield 71% (0.166 g). 1H NMR (300 MHz, CDCl3):δ=8.05 (d, J=7.2 Hz, 2H), 7.59-7.52 (m, 1H), 7.47-7.40 (m, 2H),4.32 (t, J=6.7 Hz, 2H), 1.82-1.71 (m, 2H), 1.48-1.20 (m, 10H), 0.89(t, J=6.6 Hz, 3H). 13C NMR (75 MHz, CDCl3): δ=166.70, 132.77,130.57, 129.53, 128.31, 65.16, 31.80, 29.26, 29.20, 28.74, 26.06,22.64, 14.09. GC tR=13.56 min. LRMS (EI) m/z (rel. int. %) 234[M]+(1), 123 (100), 105 (80), 84 (15), 77 (37), 55 (10), 41 (10). These data are in accordance to previous literature report (Barry et al.,1985).
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YieldReaction ConditionsOperation in experiment
97.9% With 1-(tert-butyl)-2-(chlorobenzyl) azodicarboxylate; triphenylphosphine; In dichloromethane; at 0 - 20℃; for 4h; General procedure: A solution of azo-reagent (1.2 mmol) in THF or CH2Cl2 (3 mL) was added slowly to the solution of alcohol (1 mmol), acidic pronucleophile (1.2 mmol) and Ph3P (1.2 mmol) in THF or CH2Cl2 (5 mL) at 0-5 C and the reaction mixture was continued stirring a troom temperature. The reaction was monitored by TLC. The solution was concentrated and the toluene was added. The 1-(tert-butyl)2- (4-chlorobenzyl) hydrazinedicarboxylate (4a) precipitated and was filtered off. Then the filtrate was evaporated under reduced pressure. The product was purified by column chromatography on silica gel to afford the pure products.
95% With dmap; 2,6-dichloro-4-(perfluorohexyl)benzoyl chloride; N-ethyl-N,N-diisopropylamine; In benzene; at 25℃; for 1h; A mixture of benzoic acid (60 mg, 0.49 mmol), N,N-diisopropylethylamine (78 mg, 0.60 mmol), FY reagent 1a (290 mg, 0.55 mmol) and N,N-dimethylaminopyridine (DMAP, 72 mg, 0.59 mmol) in benzene (3 mL) was stirred at 25 C for 15 min. 1-Octanol (77 mg, 0.59 mmol) was added, and the mixture was stirred at room temperature for 1 h. Brine (10 mL) was then added to the mixture, which was poured into iced water (20 mL) to precipitate a white solid. The precipitate was separated, and the filtrate was washed with brine (2*5 mL), dried over Na2SO4 (3 g) and concentrated in vacuo. The crude residue was purified by silica gel (10 g) chromatography with hexane/chloroform=1/1 as the eluent to give n-octyl benzoate (109 mg, 95%) as a colourless liquid; 1H NMR (500 MHz, CDCl3) δ 0.88 (t, J=7.3 Hz, 3H), 1.25-1.45 (m, 10H), 1.77 (quint, J=6.9 Hz, 2H), 4.32 (t, J=6.9 Hz, 2H), 7.44 (t, J=7.8 Hz, 2H), 7.56 (t, J=7.4 Hz, 1H), 8.05 (d, J=6.9 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ 14.1, 22.6, 26.0, 28.7, 29.2 (2C), 31.8, 65.1, 128.3, 129.5, 130.5, 132.8, 166.7. The white precipitate obtained by the filtration was poured into a 2 M HCl solution (10 mL) and the mixture was extracted with diethyl ether (3*10 mL). The combined organic layer was washed with brine (2*15 mL) and dried over Na2SO4 (5 g) and concentrated in vacuo to recover fluorous-benzoic acid 9a (247 mg, 89%) as a pale yellow solid.
91% With sulfonated polypyrene; In n-heptane; at 110℃; for 10h; General procedure: The mixture of 3-phenylpropionic acid (300 mg, 2.0 mmol), 1-octanol (260 mg, 2.0 mmol), and S-PPR (50 mg) in heptane (4 mL) was stirred at 110 C for 2 h in a 10 mL pear-shaped round-bottom flask (Shibata, SPC-15 joint) equipped with a Liebig condenser. S-PPR was removed by filtration. The filtrate was evaporated (40 C) under reduced pressure. The residue was purified by column chromatography (hexane/ethyl acetate = 20:1) to give octyl 3-phenylpropionate (515 mg, 98%) (Table 3, entry 1).
91% With N-butyl-2,4-dinitroanilinium p-toluenesulfonate; In 2,2,4-trimethylpentane; for 24h;Reflux; General procedure: The mixture of a carboxylic acid (2 mmol) and an alcohol (2 mmol) in 4 mL of iso-octane was treated with a various amount of catalyst at a various temperature. GC analyses were employed to monitor the reaction progress. Then, the solvent was removed and the crude mixture was applied onto a flash chromatography to yield a pure final product. A mixture of ethyl acetate and hexane was typically used for flash chromatography purification.
81% With high p-toluenesulfonate content diphenylamine and terephthalaldehyde resin; In neat (no solvent); at 110℃; for 48h; General procedure: A mixture of 3-phenylpropionic acid (300 mg, 2.0 mmol), 1-octanol (260 mg, 2.0 mmol), and DTRT(H) (171 mg) was heated at 110C for 8 h. Removal of DTRT(H) by filtration followed by evaporation of the filtrate at 40C under reduced pressure gave aresidue that was purified by column chromatography (hexane:EtOAc D 20:1) to give 11 (482 mg, 92%). The catalyst which was separated by filtration was used for the next experiment.
65% With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; at 70℃; for 20h; General procedure: The mixture of carboxylic acid, alcohol, and 1,3-dibromo-5,5-dimethylhydantoin was stirredin a 25 mL reactor tube at 70 C for 2-40 h. After reaction completion, the mixture was cooled toroom temperature and the alcohol was evaporated under reduced pressure. The isolation procedurewas as follows, except where noted dierently in the Supporting Information. The residue wasdissolved in 10 mL ethyl acetate and washed with a mixture of 1 mL saturated NaHCO3(aq), 1 mLsaturated Na2S2O3(aq), and 10 mL distilled water, and the water phase was extracted with ethyl acetate(2 10 mL). The organic layers were combined, dried over Na2SO4, and the solvent was evaporatedunder reduced pressure.
57% With N-Bromosuccinimide; at 70℃; for 20h; General procedure: The mixture of carboxylic acid, alcohol and N-bromosuccinimide was stirred in a 25 mL reactortube at 70 C for 2-40 h. After the completion of the reaction, the mixture was cooled to roomtemperature and alcohol was evaporated under reduced pressure. The isolation procedure was as follows, except where noted differently in Section 3.2.6. The residue was dissolved in ethyl acetate andconsecutively washed with 10 mL of 10% Na2S2O3 (aq), 5 mL of saturated NaHCO3 (aq) and 10 mL ofdistilled water. The water phase was extracted with ethyl acetate (3Χ5 mL). The organic layers were combined, dried over Na2SO4 and the solvent was evaporated under reduced pressure.
33% With 2-oleamido-5-nitro-pyridinium p-toluenesulfonate; In 2,2,4-trimethylpentane; for 144h;Reflux; General procedure: A catalyst ranging from 1-10 mol% was added to a mixture of an acid (1 eq.) and an alcohol (1 eq.) in isooctane (4mL). The resultant reactions were carried out at various temperatures and the reaction progresses were monitored by GC and TLC analyses. Then, the solvent was removed in vacuo and the products were isolated, purified by flash chromatography, and characterized by 1H NMR, 13C NMR, IR, and high-resolution mass spectrometry.
With dmap; 2-chloro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluorododecyl)pyridinium trifluoromethanesulfonate; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 1h; General procedure: To a solution of benzoic acid (62.8 mg, 0.51 mmol), aniline (47 μl, 0.51 mmol) and DMAP (62.8 mg, 0.51 mmol) in dry DMF (8 ml) was added the fluorous Mukaiyama reagent 3d (500 mg, 0.61 mmol) at room temperature. The reaction mixture was stirred for 1 h at ambient temperature. After the addition of H2O (2 ml), the reaction mixture was stirred for an additional 5 min and then filtered. After washing the precipitate with 20% aq DMF (10 ml), 1.0 M HCl was added to the filtrate, which was then extracted with diethyl ether. The organic layer was then washed again with1.0 M HCl and brine. After drying the organic layer with Na2SO4, concentration of the organic phase provided the coupling product in quantitative yield (101 mg), in high purity (99%).
88%Chromat. With toluene-4-sulfonic acid; trimethylcyclohexylammonium p-toluenesulfonate; at 80℃; for 4h; General procedure: Equimolar amounts of quaternary ammonium salt (1.5 mmol) and p-toluenesulfonic acid monohydrate (Sigma-Aldrich, 98,5+% used as received) were mixed in a screw-capped 3 ml vial. The mixture was magnetically stirred and heated to 60 C until a clear colourless liquid was obtained (about 10 min). DES was used right after its preparation. Equimolar amounts (4.5 mmol) of acid and alcohol were added, and the resulting mixture, was heated to 60 C (or 80 C if specified) and magnetically stirred for the specified amount of time. Initially the reaction mixture is homogeneous and fluid, and then a heterogeneous system formed as reaction proceeded, due to insolubility of the esters produced in the DES. For the g.c. analysis further elaboration was as follows. At the end of the reaction, tbutylbenzene was added, as the internal standard, to the mixture, which was then extracted with diethyl ether. Organic layer was washed with NaHCO3, dried over Na2SO4 and analyzed by g.c.
98%Chromat. With poly(ethylene glycol) 1000 based dicationic acidic ionic liquid; In toluene; at 80℃; for 1h;Ionic liquid; General procedure: Aromatic acids (2 mmol) and alcohols (3 mmol) were added into a 10 mL tube reactor preloaded with PEG1000-DAIL (2 mL) and toluene (2 mL). The reaction mixture was stirred thoroughly at 80C for 1 h. After the completion of reaction, the mixture separated into two phases at room temperature, the upper phase was decanted for analysis and the below phase was reused for the next time directly or after removing water under vacuum at 80C for 1 h.

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YieldReaction ConditionsOperation in experiment
82% With lithium hexamethyldisilazane; In neat (no solvent); at 0 - 20℃; for 3h; General procedure: Ester (1 mmol) and alcohol (3 mmol) were added in a round bottom flask, followed by the addition of base LiHMDS (2 mmol) at 0 C. The reaction was stirred at room temperature for about 3 h. The reaction was monitored by TLC. After completion of the reaction, ethyl acetate was added to the reaction mixture and washed with water three times. The ethyl acetate layer was evaporated on the rota evaporator, and the crude products were purified by column chromatography in pet ether.
80% With high p-toluenesulfonate content diphenylamine and terephthalaldehyde resin; In neat (no solvent); at 110℃; for 48h; General procedure: A mixture of methyl 3-phenylpropionate (328 mg, 2.0 mmol), 1-octanol (390 mg, 3.0 mmol), and DTRT(H) (171 mg) was stirred at 110C for 4 h. The mixture was treated in a manner similar to the procedure described above to give 11 (493 mg, 94%).
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