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CAS No. : | 103-54-8 | MDL No. : | MFCD00008722 |
Formula : | C11H12O2 | Boiling Point : | - |
Linear Structure Formula : | C6H5C3H4OCOCH3 | InChI Key : | WJSDHUCWMSHDCR-VMPITWQZSA-N |
M.W : | 176.21 | Pubchem ID : | 5282110 |
Synonyms : |
3-Phenylallyl acetate
|
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: |
* 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 |
---|---|---|
>= 99% | With C40H56N2RuSi4; hydrogen; In toluene; at 25℃; under 7600.51 Torr; for 6h;Schlenk technique; Autoclave; | A magnetic stirrer was placed in a 20 mE Schlenk tube and the tube was dried by heating under a reduced pressure of 5 Pa, after which the tube interior was purged with argon. Ruthenium Complex C (7.7 mg, 0.010 mmol) was added as the catalyst to this Schlenk tube and dissolved in toluene (2 mE). To this solution was added cinnamyl acetate (176 mg, 1 .0 mmol). The resulting solution was transferred to an autoclave and the interior of the autoclave was purged with hydrogen. Next, the solution was stirred for 6 hours at roomtemperature under a hydrogen atmosphere at a pressure of 10 atmospheres. Anisole was added as an internal reference, the ?H-NMR spectrum was measured, and the structure and yield of the product were determined. The structure of the resulting compound was confirmed from the ?H and ?3C- NMR spectra. These results are shown as Entry 10 in Table6.?H-NMR (400 MHz, CDC13) &1.96 (m, 2H,PhCH2CH2CH2-), 2.06 (s, 3H, Me), 2.70 (m, 2H, 2H,PhCH2CH2CH2-), 4.09 (t, 2H, J6.8 Hz,PhCH2CH2CH2-), 7.17-7.23 (m, 3H, Ph), 7.27-7.32 (m,2H, Ph).?3C-NMR (100 MHz, CDC13) &21.1, 30.3, 32.3, 64.0,126.2, 128.5, 128.6, 141.3, 171.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12%Chromat.; 88%Chromat. | With sodium tetrahydroborate; 2,5% palladium on carbon; acetic acid; In toluene; at 20℃; for 1h;Inert atmosphere; | General procedure: A 25 mL round-bottomed flask with stir bar is flushed with inert gas and charged with Pd/C catalyst (2.5 mol %), the substrate (1 mmol), tert-butylbenzene (internal standard, 1 mmol), and 5 mL of toluene. The flask is clamped over a magnetic stirrer, and the contents are stirred. Acetic acid (2 mmol) is added in a single portion via pipette. Powdered NaBH4 (4 mmol) is added in a single portion directly to the stirring heterogeneous solution (Note: Addition of the NaBH4 causes the rapid evolution of small hydrogen gas bubbles. Avoid open flames). The contents of the reaction flask are left to stir in the open air at room temperature for 1 h. Workup is conducted by quenching the reaction mixture with several mLs of 0.1 M HCl until no further hydrogen evolution is observed. The solution is then made basic using NaHCO3 and the organic portion is extracted after the addition of diethyl ether. The organic layer is then dried with MgSO4 and then filtered through glass wool or celite. Reactions are analyzed by GC/MS. |