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CAS No. : | 498-02-2 | MDL No. : | MFCD00008747 |
Formula : | C9H10O3 | Boiling Point : | - |
Linear Structure Formula : | (H3CO)(HO)C6H3COCH3 | InChI Key : | DFYRUELUNQRZTB-UHFFFAOYSA-N |
M.W : | 166.17 | Pubchem ID : | 2214 |
Synonyms : |
Acetovanillone;Acetoguaiacone;NSC 209524;NSC 2146
|
Chemical Name : | 1-(4-Hydroxy-3-methoxyphenyl)ethanone |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
Apocynin (CAS: 498-02-2) can be used in the preparation of Bosutinib (SKI-606) (CAS: 380843-75-4). Bosutinib, a small molecule that inhibits BCR-ABL and src tyrosine kinases, is utilized for treating chronic myelogenous leukemia.
* 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 |
---|---|---|
The synthesis of E (Scheme 4) requires coupling of the carboxylic acid sulfosuccinimidyl ester 27, derived from 23, with 24 followed by the cleavage (TBAF, [HOAC,] THF) of the silyl protecting group . and subsequent conversion [(TSCL,.] pyr, Nal, acetone) of the alcohol into iodide 28, [ALKYLATION.] of the. phenoxide anion derived from 32 with iodide 28 gives rise to 33. Completion of the synthesis of E requires 1) reduction (NaBH4) of the methyl ketone functionality, 2) coupling of the resultant alcohol 34 with the new reagent 38 leading to 39 and 3) brief exposure of 39 to trimethyl silyl iodide, which leads, upon aqueous workup, to E. The required aromatic piece 32 is prepared from commercially available [ACETOVANILLONE] 29, as outlined in Scheme 5, using the protocol of [AKERBLOM] [(AKERBLOM,] E. [ <P>B. , ET AL., (1998) SIX NEW PHOTOLABILE LINKERS FOR SOLID-PHASE SYNTHESIS. 1. METHODS OF PREPARATION.] Mol. Divers., 3,137-148). The novel reagent 38 is prepared from the commercially available sulfo- NHS acetate 35 as detailed in Scheme 6. The methylation of sulfonate anions is well documented in the literature (Trujillo, J. L. and Gopalan, A. S. (2000) Facile [ESTERFICATION] of Sulfonic Acids and Carboxylic Acids with Triethylorthoacetate, Tetrahedron Letters 34,7355-7358), as well as the [ TREATMENT OF N-HYDROXYSUCCINIMIDE WITH BIS (BICHLOROMETHYL) CARBONATE (KONAKAHARA, T. , ET AL., (1993)] A Convenient Method for the Synthesis of Activated N-Methylcarbamates, Synthesis 103-106). | ||
With pyridine; In tetrahydrofuran; at 20.0℃; for 3.0h; | As shown in the above-described reaction formula, acetovanillone (500 mg, 3 mM) dissolved in 20 ml of THF was mixed with 0.5 ml of pyridine and 0.6 ml of anhydrous acetic acid. The mixture was stirred for 3 hours at room temperature. The resulting product was recovered with the extraction with diethylether and dried with anhydrous magnesium sulfate to remove remaining solvent. The remaining residue was performed to Silica gel column chromatography with a mobile phase (n-hexane:ethylacetate=4:1) to obtain white solid type of 4-acetyl-2-methoxyphenyl acetate (1; 625 mg).m.p: 58.7 C.;1H NMR (CDCl3): delta ppm 7.60 (d, 1H, J=1.8 Hz, H-3), 7.55 (dd, 1H, J=1.8, 8.2 Hz, H-5), 7.12 (d, 1H, J=8.2 Hz, H-6), 3.89 (s, 3H, OCH3), 2.59 (s, 3H, OCOCH3), 2.33 (s, 3H, COCH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With pyridine; In tetrahydrofuran; at 20.0℃; for 3.0h; | Reference Example 1. Preparat ion of intermedi ate (1) : 4-acetyl-2- methoxyphenyl acetate ( 1)<328>1<329><330> As shown in the above-descr ibed react ion formula, acetovani l lone(500mg , 3mM) di ssolved in 20 ml of THF was mixed wi th 0.5 ml of pyr idine and 0.6 ml of anhydrous acet ic acid. The mixture was st i rred for 3 hours at room <n="38"/>temperature. The resulting product was recovered with the extraction with diethylether and dried with anhydrous magnesium sulfate to remove remaining solvent. The remaining residue was performed to Silica gel column chromatography with a mobile phase (n-hexane:ethylacetate=4:l) to obtain white solid type of 4-acetyl-2-methoxyrhohenyl acetate (1 ; 625mg).<331> <332> m.p.: 58.7 C ;<333> 1H NMR (CDCl3) : delta ppm 7.60 (d, 1 H1 J = 1.8 Hz , H-3), 7.55 (dd, 1 H, J = 1.8, 8.2 Hz, H-5), 7.12 (d, 1 H, J = 8.2 Hz, H-6), 3.89 (s, 3 H, OCH3), 2.59 (s, 3 H, OCOCH3), 2.33 (s, 3 H, COCH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water;HUSY (Si/Al=15); at 250℃; under 5250.53 Torr; for 2h;Inert atmosphere;Product distribution / selectivity; | In an autoclave (batch reactor) lignin (0.5 g), HUSY (Si/Al=15) (0.5 g) and mixture of water and organic solvent (30 g) were charged. After flushing the reactor with nitrogen gas for 3 times, nitrogen (7 bar) was charged. Reactor was heated up to 230° C. under the stirring (100 rpm). After attaining the desired temperature of 230° C. stirring was increased up to 500 rpm. Reaction was stopped after 30 minutes. Analysis of reaction mixture was done by GC, GC-MS. The lignin used in these examples were organosolv or dealkaline.Yield: >25percentMass balance: >90percent.The effect of reaction temperature and reaction time on depolymerization reaction is demonstrated by the results presented in Table 8 using SiO2-Al2O3 as catalyst*. TABLE 8 Exp. Time Lignin Product yield, Mass balance, No. (min.) conversion percentpercentNo. percent 1. 30 85 26 80 2. 60 85 41 86 3. 90 92 50 84 4. 120 95 70 85 Lignin, 0.5 g; HUSY (Si/Al = 15), 0.5 g; N2 Pressure, 7 bar (at)RT; Temperature, 250° C.No.Monomer and dimer products soluble in water/organic solvents. |