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CAS No. : | 122-97-4 | MDL No. : | MFCD00002950 |
Formula : | C9H12O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VAJVDSVGBWFCLW-UHFFFAOYSA-N |
M.W : | 136.19 | Pubchem ID : | 31234 |
Synonyms : |
|
Chemical Name : | 3-Phenyl-1-Propanol |
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 |
---|---|---|
a. 3-Phenyl Propyl Acetate Using the procedure outlined in Example 16, 3-phenyl propanol was converted to 3-phenyl propyl acetate. | ||
(a) 3-Phenyl Propyl Acetate Using the procedure outlined in Example 16, 3-phenylpropanol was converted to 3-phenyl propyl acetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
440 mg | (1) Sodium hydride (99 mg, 4.14 mmol) was added to a solution of 3-phenyl-1-propanol (564 muL, 4.14 mmol) in N,N-dimethylformamide (15 mL) while cooling in ice, and the mixture was stirred for 30 min while cooling in ice. A solution of <strong>[456-24-6]2-fluoro-5-nitropyridine</strong> (500 mg, 3.45 mmol) in N,N-dimethylformamide (5 mL) was added thereto. The mixture was warmed to room temperature and stirred for 19 hr. Subsequently, sodium hydride (99 mg, 4.14 mmol) was added thereto and the mixture was stirred at room temperature for 2 hr. Thereafter, the mixture was heated to 85°C, stirred for 1.5 hr, and further stirred at room temperature for 2 hr. Water was added to the reaction mixture while cooling in ice, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid and dried over anhydrous magnesium sulfate. The desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 19:1) to afford 5-nitro-2-(3-phenylpropoxy)pyridine as a brown solid (440 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane;Sealed tube; Inert atmosphere; | To a 50 mL roundbottom flask containing a stir bar was added 1- ((benzyloxy)carbonyl) (L')-r peri di ne-2-carboy 1 i c acid (0.523 g, 1.98 mmol), followed by DCM (20 mL). To the reaction vessel was added (in the order listed) EDCI (0.45 g, 2.5 mmol), TEA (0.696 mL, 0.505 g, 5.0 mmol), and DMAP (0.060 g, 0.50 mmol). The reaction vessel was sealed and flushed with nitrogen. Stirring commenced and 3 -phenyl- 1 -propanol was added via syringe (0.258 mL, 0.258 g, 1.9 mmol). The reaction was allowed to proceed overnight. The following day, the reaction was transferred to a separatory funnel in which it was washed with water (10 mL), dilute HC1 (10 mL 0.5 M HC1), saturated aqueous sodium bicarbonate (20 mL) and brine. The crude product was dried over sodium sulfate and concentrated to dryness in vacuo. The crude product was purified by silica gel (0439) chromatography (1 :4 ethyl acetate: hexanes, R/= 0.30) to yield the pure product as a clear oil (0.276 g, 38 %). NMR (500 MHz) (CDCb) (amide rotamers) d: 7.35 - 7.13 (10H, m), 5.16 - 5.13 (2H, m), 4.97 - 4.85 (1H, m), 4.15 - 4.05 (3H, m), 3.10 - 2.94 (1H, m), 2.68 - 2.61 (2H, m), 2.27 - 2.19 (1H, m), 1.98 - 1.89 (2H, m), 1.71 - 1.62 (3H, m), 1.47 - 1.41 (1H, m), 1.29 - 1.21 (1H, m). 13C NMR (125 MHz) (CDCb) (amide rotamers) d: 171.6, 156.5, 155.4, 141.0, 136.6, 128.4, 128.4, 127.9, 127.8, 126.0, 67.3, 67.2, 64.3, 54.6, 54.4, 41.9, 41.8, 32.0, 26.8, 26.7, 24.7, 24.5, 20.7, 20.6. HRMS calc?d for [M+H] = 382.2018, observed = 382.2044. IR (NaCl, DCM): 3028, 2943, 2860, 1737, 1710, 1454, 1417, 1336, 1255, 1255, 1203, 1163, 1090, 1044. |