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CAS No. : | 14262-60-3 | MDL No. : | MFCD00055949 |
Formula : | C18H20O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 316.35 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | N/A | |
Precautionary Statements: | UN#: | N/A | |
Hazard Statements: | Packing Group: | N/A |
* 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 |
---|---|---|
In methanol for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In butan-1-ol at 120℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With potassium hydroxide In dimethyl sulfoxide for 0.0833333h; Microwave irradiation; | Symmetric DBC: Dibenzo-14-crown-4 Ether (2) General procedure: Prepared using general procedure 2, re-crystallized in methanol. Yields (Open vessel, std. temp control mode: 35%,power/time mode: 13%; Closed vessel, std temp control:54%, power/time mode: 60%). White crystals. Melting point:148-150°C, (Lit.[2] 150-152°C). IR (KBr disc cm-1): 1040-1120 (-CO). 1H NMR (400 MHz, CDCl3) (ppm): 2.26 (q,4H, J=5.6 Hz, -CH2-), 4.24 (t, 8H, J=5.6 Hz, -CH2-), 6.89-6.91 (m, 8H, aromatic). 13C NMR (100 MHz, CDCl3)(ppm): 29.28, 67.32, 115.58, 121.72, 149.44. Anal. Calc. forC18H20O4: C, 71.98; H, 6.71; O, 21.31. Found: C, 72.39; H,6.25; O, 21.36. The 2-step MW was performed similarly but using the diphenol intermediates in lieu of catechol as precursor. Either symmetric or asymmetric DBCEs (2-6) can be obtained through this method depending on the alkyl dihalide used for the ring closure reaction. |
With sodium hydroxide 1) isoamyl alcohol, boiled , water trap, 2) 10 h, boiled; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With potassium hydroxide In dimethyl sulfoxide at 90℃; for 2.5h; | |
With sodium hydroxide 1) butanol, water, reflux, 2) butanol, water, reflux, 20 h; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With hydrogen; acetic acid In butan-1-ol at 110℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / dimethyl sulfoxide / 0.08 h / Microwave irradiation 2: potassium hydroxide / dimethyl sulfoxide / 0.08 h / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran addn. of an anhydrous THF soln. of the crown-ether to UI3 in anhydrous THF;; washed twice with THF; dried in a stream of argon;; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With BF3-Et2O In water To a soln. of dibenzo-15-crown-5 in BF3-Et2O aq. soln. (containing H2(17)O (17O atom%=10)) of CuSO4 was added at room temp.;; detected by UV-spectroscopy;; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With H2O; BF3-Et2O In water To a soln. of crown-ether in BF3-Et2O aq. CuSO4 was added at room temp.;; detected by UV-spectroscopy;; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform CuCl2 (preheated at 100°C for 6 h) mixed with crown ether in dryCHCl3 under vac.; product not isolated, detected by ESR; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol stoich. amts., heating; filtration, crystn. on cooling or slow evapn. (room temp.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethyl acetate stoich. amts., heating; filtration, crystn. on cooling or slow evapn. (room temp.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | In melt (N2); using Schlenk techniques; addn. of RuCl2(η6-C6H5CO2Et) to meltof dibenzo-15-crown-5 at 150°C; stirring for 10 min; cooling to room temp., extn. of residue with H2O; removal of solvent, redissolving in CHCl3, filtration, pptn. by addn. of Et2O; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | Stage #1: bis(2-hydroxyphenoxyethyl)ether With caesium carbonate In acetonitrile for 3h; Reflux; Inert atmosphere; Stage #2: 1,2-bis(methanesulfonyloxy)ethane In acetonitrile Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: 1,2-bis(o-hydroxyphenoxy)ethane With caesium carbonate In acetonitrile for 3h; Reflux; Inert atmosphere; Stage #2: diethylene glycol dimesylate In acetonitrile Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,2-dichloro-ethane Flash photolysis; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With potassium fluoride In acetonitrile for 24h; | 2.2. General procedure for synthesis of complexes of dibenzo-15-crown-5(6,7,9,10,17,18-hexahydrodibenzo [b,h] [1,4,7,10,13] with potassium halides General procedure: Solutions of dibenzo-15-crown-5 and potassium salt in acetonitrile were mixed in 1:10M ratio and the solution was stirred for 24 h. The solution was filtered and the solvent was evaporated. The solid was extracted with minimum amount of nitromethane. Purity was checked by TLC. In case of a mixture, the product was again washed with 2 ml:3ml petroleum ether:1,2-dichloroethane solvent mixture to remove unreacted dibenzo-15-crown-5 and the complex was obtained as residue.The complexes were dried under vacuum and stored in a vacuum desiccator over fused calcium chloride. The melting point was recorded for each complex. 1. [(Dibenzo-15-crown-5)2K+]F-: Mol. Formula C36H40O10KF, Yield:87%, M.pt. 120 °C, CHN %: calculated C:31.30, H:2.89, N:0 experimental:C:30.24, H:2.18, N: 0; 1H NMR/ppm (400 MHz, CDCl3):6.95-6.92 (m, J=4.8 Hz, 4.0 Hz, 0 Hz, 16H), 4.37 (s, 8H), 4.20 (q,J=5.2 Hz, J=4.4 Hz, J=13.2 Hz, 8H), 3.94 (p, J=5.6 Hz,J=5.2 Hz, J=4.4 Hz, J=4.4 Hz, 8H); 13C NMR/ppm (100 MHz,CDCl3): 148.15 (PhC), 147.90 (PhC), 123.12 (Ar-C), 122.72 (CH),121.39 (Ar-C), 116.11 (Ar-C), 115.04 (Ar-C), 114.71 (Ar-C), 69.91(CH2), 69.17 (CH2), 67.91 (CH2); ESI m/z: [L+K]: 355, calculated355, [(2L+K]+:671, calculated 671; IR max/cm-1: 3059 (w), 2923(s), 2856 (m), 1588 (s),1496 (m), 1453 (m), 1389 (w), 1251 (s),1208 (s), 1120 (s), 1041 (s), 928 (m), 745 (s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With potassium chloride In acetonitrile for 24h; | 2.2. General procedure for synthesis of complexes of dibenzo-15-crown-5(6,7,9,10,17,18-hexahydrodibenzo [b,h] [1,4,7,10,13] with potassium halides General procedure: Solutions of dibenzo-15-crown-5 and potassium salt in acetonitrile were mixed in 1:10M ratio and the solution was stirred for 24 h. The solution was filtered and the solvent was evaporated. The solid was extracted with minimum amount of nitromethane. Purity was checked by TLC. In case of a mixture, the product was again washed with 2 ml:3ml petroleum ether:1,2-dichloroethane solvent mixture to remove unreacted dibenzo-15-crown-5 and the complex was obtained as residue.The complexes were dried under vacuum and stored in a vacuum desiccator over fused calcium chloride. The melting point was recorded for each complex. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With potassium bromide In acetonitrile for 24h; | 2.2. General procedure for synthesis of complexes of dibenzo-15-crown-5(6,7,9,10,17,18-hexahydrodibenzo [b,h] [1,4,7,10,13] with potassium halides General procedure: Solutions of dibenzo-15-crown-5 and potassium salt in acetonitrile were mixed in 1:10M ratio and the solution was stirred for 24 h. The solution was filtered and the solvent was evaporated. The solid was extracted with minimum amount of nitromethane. Purity was checked by TLC. In case of a mixture, the product was again washed with 2 ml:3ml petroleum ether:1,2-dichloroethane solvent mixture to remove unreacted dibenzo-15-crown-5 and the complex was obtained as residue.The complexes were dried under vacuum and stored in a vacuum desiccator over fused calcium chloride. The melting point was recorded for each complex. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium iodide In acetonitrile for 24h; | 2.2. General procedure for synthesis of complexes of dibenzo-15-crown-5(6,7,9,10,17,18-hexahydrodibenzo [b,h] [1,4,7,10,13] with potassium halides General procedure: Solutions of dibenzo-15-crown-5 and potassium salt in acetonitrile were mixed in 1:10M ratio and the solution was stirred for 24 h. The solution was filtered and the solvent was evaporated. The solid was extracted with minimum amount of nitromethane. Purity was checked by TLC. In case of a mixture, the product was again washed with 2 ml:3ml petroleum ether:1,2-dichloroethane solvent mixture to remove unreacted dibenzo-15-crown-5 and the complex was obtained as residue.The complexes were dried under vacuum and stored in a vacuum desiccator over fused calcium chloride. The melting point was recorded for each complex. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trifluoroacetic acid / 24 h / 90 °C / Inert atmosphere 2: aminosulfonic acid / dimethyl sulfoxide / 4 h / 95 °C / Green chemistry |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With trifluoroacetic acid at 90℃; for 24h; Inert atmosphere; | Synthesis of 4, 4 -diformyl dibenzo-15-crown-5 ether (4) Duff formylation of dibenzo-15-crown-5: The mixture of dibenzo-15-crown-5 (0.948g, 3 mmol), trifluoracetic acid (5 mL) and hexamethylene tetraamine (1.68 g, 12 mmol) was stirred at 90 °C under nitrogen for 24 hrs. The mixture was then extracted with 25 ml benzene and dried over magnesium sulphate. The concentration of the benzene extract under vacuum gave a brown oil, which on cooling solidified to white crystalline solid (4), Yield 0.756 g; (68%), M.P. 76-78 °C. |