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CAS No. : | 14615-72-6 | MDL No. : | MFCD00075777 |
Formula : | C21H18O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CHUAMRVJSRBRHT-UHFFFAOYSA-N |
M.W : | 318.37 | Pubchem ID : | 561351 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
93% | With sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1 h; | To a solution of 3,5-bis(benzyloxy)benzyl alcohol [2] (9.9 g, 31.0 mmol) in CH2Cl2 (140mL) was added DMSO (22 mL, 0.31 mol) and diisopropylethylamine (26.92 mL, 0.154mol). The mixture was cooled to 0 °C and SO3•pyridine (14.76 g, 92.73 mmol) added. The reaction stirred at 0 °C for one hour, after which it was quenched with saturated aqueous Na2S2O3 (310 mL). The solution was extracted with ethyl acetate (3 x 200 mL)and the organic layers combined and dried over MgSO4. Evaporation of the solvent afforded an oil which was purified by silica gel column chromatography in CH2Cl2 to give 9.2 g (93percent) of the desired product. The spectra was similar to data reported previously [3]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate In acetone at 0 - 40℃; for 12 h; Inert atmosphere | General procedure: To the stirred solution of phenolic aldehyde (2.00 mmol) in anhydrous acetone (10 mL) was added K2CO3 (3.00 mmol, 1.5 eq.) In a nitrogen atmosphere0 And cooled.Benzyl bromide (2.4 mmol, 1.2 eq.) Was slowly added,The mixture temperature was raised to 40 ,Stir for 12 hours.After completion of the reaction, the reaction mixture was cooled to room temperature,Filter through a Celite pad and concentrate in vacuo.The crude compound was purified by column chromatography (EtOAc / Hexane = 1/3) to give the pure aromatic aldehyde in which the benzyl group was protected [note: two equivalents of K2CO3 were used in the synthesis of compound 18, 2.4 equivalents of benzyl bromide and 4.0 equivalents of K2CO3 was used for the synthesis of Compound 19). |
82% | With potassium carbonate; potassium iodide In acetone at 20℃; for 4 h; Inert atmosphere | A stirred suspension of 3,5-dihydroxybenzaldehyde (690mg, 5mmol), potassium carbonate (3.46g, 25mmol) and potassium iodide (166.0mg, 1mmol) in acetone (15mL) was treated dropwise with benzyl bromide (1.18mL, 10mmol) and stirring continued for 4h at room temperature. The resulting suspension was concentrated under reduced pressure and the crude mass subjected to flash column chromatography (silica, 4:1 v/v hexane/ethyl acetate) and concentration of the relevant fractions (Rf=0.58 in 4:1 v/v hexane/ethyl acetate) afforded the title compound as a white powder (1.3g, 82percent) m.p. 80–81°C. (0031) 1H NMR (DMSO-d6, 500MHz): δ 9.91 (s, 1H), 7.48–7.44 (m, 4H), 7.43–7.38 (m, 4H), 7.37–7.32 (m, 2H), 7.17 (d, J=2.3Hz, 2H), 7.01 (t, J=2.3Hz, 1H), 5.17 (s, 4H) ppm. 13C NMR (DMSO-d6, 126MHz): δ 192.6, 159.9, 138.3, 136.6, 128.4, 127.9, 127.7, 108.2, 108.1, 69.6ppm. IR (diamond cell, neat) νmax: 1686, 1591, 1447, 1381, 1349, 1296, 1170, 1048, 829, 739, 719, 694, 675, 629cm−1. LRMS (+ESI) m/z: 319 [(M+H)+, 100percent] |
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