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CAS No. : | 32596-43-3 | MDL No. : | MFCD00067051 |
Formula : | C8H5ClO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MYHXSDYZVOKOAT-UHFFFAOYSA-N |
M.W : | 184.58 | Pubchem ID : | 122912 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501 | UN#: | N/A |
Hazard Statements: | H302-H312-H332 | 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 |
---|---|---|
With potassium carbonate; In N-methyl-acetamide; water; | 1) A mixture of <strong>[32596-43-3]2,6-diformyl-4-chlorophenol</strong> (1.0 g, 5.4 mmol), 8-phenyloctyl chloride (1.35 g, 6 mmol) and anhydrous potassium carbonate (0.83 g, 6 mmol) in dry dimethylformamide was heated to 140 C. for 6 hours. After cooling to room temperature, water (29 ml) was added and the mixture extracted with ethyl acetate (20 ml). The extracts were washed with 2M sodium hydroxide (2*10 ml), water (10 ml), dried, filtered and evaporated to a brown oil. Chromatography on flash silica eluding with diethyl ether gave 5-chloro-2-(8-phenyloctyloxy)-3-benzenedicarboxaldehyde as a pale yellow oil (2 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile dropwise addn. of amine to 2 equiv. aldehyde, refluxinf with 1 equiv. La(NO3)3 for 3 h, standing for 3 h; evapn., treatment with CHCl3, collection (filtration), washing (CHCl3), drying (vac.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | In ethanol; at 20℃; for 4h; | To the solution of <strong>[32596-43-3]2,6-diformyl-4-chlorophenol</strong> (1.845 g, 10 mmol) in absolute ethanol (10 mL), the ethanol solution (15 mL) of ethylenediamine (0.3 g, 5 mmol) was added dropwise, the orange deposit appeared. The mixture was stirred at room temperature for 4 h. Then the resulting solution was filtered, the precipitate was washed with ether and absolute ethanol several times and dried in vacuo. Yield: 1.12 g (57%). Anal. Calc. For C18H14Cl2N2O4 (%): C, 54.98; H, 3.59; N, 7.12. Found: C, 54.64; H, 3.22; N, 7.53. IR (KBr, ν/cm-1): 3040, 2926 ν (C-H), 1645 ν (C=N), 1683 ν (C=O), 1221, 1042 ν (C-O). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In ethanol;Reflux; | General procedure: The Schiff-base was prepared by condensation reaction betweenan aldehyde and a primary amine. An ethanolic solution(10 mL) of 3-amino-4-hydroxy benzoic acid (10 mmol) was addeddropwise to an ethanolic solution (15 mL) of 2,6-diformyl-4-methyl-phenol (10 mmol) with constant stirring. The resultantmixture was refluxed for 6 h and the solvent was reduced by rotaryevaporator. The solid mass thus obtained was recrystallised severaltimes from dry ethanol to get the pure ligand. 1H NMR (300 MHz, DMSO-d6, 25 C) d = 15.105 (s, 1H, COOH),14.730 (br, 1H, OHa), 10.392 (s, 1H, CHO), 10.285 (br, 1H, OHb),9.049 (s, 1H, NH), 7.995 (s, 1H, Hc), 7.806, 7.804 (sb, He), 7.767 (s,1H, Hd), 7.561, 7.558 (d, Hf), 7.018, 7.001 (d, Hg).FT IR m (KBr) [cm 1] = 1680(s), 1629(s), 1528(s), 1384(s).ESI-MS m/z = 320.7762 (calculated for 12C15H10NO5Cl + H+:320.7049). |
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