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CAS No. : | 134-96-3 | MDL No. : | MFCD00006943 |
Formula : | C9H10O4 | Boiling Point : | - |
Linear Structure Formula : | C6H2CHO(OH)(OCH3)2 | InChI Key : | - |
M.W : | 182.17 | Pubchem ID : | - |
Synonyms : |
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Chemical Name : | 4-Hydroxy-3,5-dimethoxybenzaldehyde |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
In ethanol; at 70 - 80℃; for 3h; | General procedure: The mixture of <strong>[78364-55-3]6-fluoro-2-hydrazinylbenzo[d]thiazole</strong> (2) (0.01 mol) and benzalde-hyde/substituted benzaldehyde (0.01 mol) was reuxed in ethanol (15 ml) at 70?80 °C for 3 h. The separated product obtained was ltered off, washed withdistilled water and recrystallized from methanol to give the correspondinghydrazone. The product obtained was further dissolved in acetic acid (20 ml) atroom temperature followed by the addition of sodium acetate (0.5 g). Bromine(2 mmol) in acetic acid (10 ml) was added dropwise to the reuxing reactionmixture. After 1 h, the mixture was poured onto crushed ice (100 g). The precipitateobtained was ltered off and crystallized from ethanol-dimethylformamide (1:1) togive crystals of (3a?3t). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With copper; In N,N-dimethyl acetamide; at 200℃; for 4h;Sealed tube; Inert atmosphere; | A mixture of syringaldehyde (550 mg, 3.0 mmol), 4-bromo-3-methoxy-benzadehyde (1610 mg, 7.5 mmol), copper powder (1140 mg, 18 mgatom, 99.5percent purity) and N,Ndimethylacetamide (7.5 mL) was heated to 200°C in a sealed tube under an N2 atmosphere for 4 h with stirring. The cooled mixture was then filtrated; the filtrate was poured into water and extracted three times with CH2Cl2. The combined organic layers were washed with brine and dried over Na2SO4. Evaporation of the solvent and purification of the residue by column chromatography (n-hexane/ethyl acetate = 4:1) on silica gel yielded dialdehyde 8 (280 mg,0.87 mmol, 29percent) as a pale yellow oil. IR vmax (diamond ATR) cm?1: 2948, 1690, 1676, 1633,1598, 1489, 1462, 1332, 1226 and 1026. 1H NMR delta (400 MHz in CDCl3): 3.82 (3H, s), 3.87 (6H,s), 6.58 (1H, d, J = 9.1 Hz), 6.98 (1H, dd, J = 9.1, 3.2 Hz), 7.21 (2H, s), 7.38 (1H, d, J = 3.2 Hz), 9.95(1H, s), 10.70 (1H, s). 13C NMR delta (100 MHz in CDCl3): 55.8, 56.4, 106.5, 109.5, 116.7, 123.3, 125.5,133.7, 153.9, 154.9, 155.2, 189.5, 190.9. HRFAB?MS m/z [M + H]+: Calcd. for C17H17O6: 317.1025,found: 317.1025. |