Structure of 155697-42-0
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 155697-42-0 |
Formula : | C16H16O2 |
M.W : | 240.30 |
SMILES Code : | OC/C=C/C1=CC=CC(OCC2=CC=CC=C2)=C1 |
MDL No. : | MFCD22041864 |
InChI Key : | QQGGFBBEVHNLKT-WEVVVXLNSA-N |
Pubchem ID : | 86687335 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 |
* 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 |
---|---|---|
98.2% | Example 5Preparation of (2£)-3-(3-benzyloxyphenyl)prop-2-en-l-ol (general formula IV: R = CH2Ph); A solution of 103.1 g (0.365 mol) of ethyl-3 '-benzyloxy-E cinnamate in dry toluene (730 ml) is cooled in an ice bath (ice + salt) under argon atmosphere to - 10C, and then, a 1 M solution of diisobutylalane in toluene is added dropwise (temperature range -5 to 0C) within 50 min. The yellowish solution is stirred at about -3C for 2.5 h; the course of the reaction is checked using TLC, the cooling is switched off, and slow stirring continues overnight.The reaction mixture cooled in an ice bath to 5C is added gradually under stirring to 500 ml of a cooled saturated solution of ammonium chloride. Then, 1 N hydrochloric acid (500 ml) and, thereafter, concentrated hydrochloric acid (145 ml) are added. Methyl tert-butyl ether (MTBE; 400 ml) is added and the mixture is stirred for another 30 minutes. The aqueous phase is separated and shaken with MTBE (400 ml, 150 ml). The combined organic portions are washed with 0.5 N sodium hydroxide (380 ml), water (380 ml), and brine (350 ml). After filtration, the solution is evaporated in a rotating vacuum evaporator, during which a product crystallizes. 86.17 g (98.2 %) of the alcohol of general formula II: R = CH2Ph) is obtained, sufficiently pure for using in the following step, melting point = 60.2 - 63.7C.-NMR (CDCI3) δ 1.40 (1 H, bs), 4.32 (2H, d, J = 5.6 Hz), 5.08 (2H, s), 6.35 (1 H, dt, J = 5.6, 15.9 Hz), 6.59 (1 H, d, J = 15.9 Hz), 6.88 (1H, dd, J = 2.5, 8.3 Hz), 6.98-7.01 (2H, m), 7.20-7.39 (6H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.7% | carbon tetrabromide; at 62℃; for 10.3333h;Inert atmosphere; | Example 3Preparation of (2£')-3-(3-benzyloxyphenyl)prop-2-en- l -yl-propionate (general formula III: R = CH2Ph); Propionic anhydride (49.2 ml, 0.384 mol) is added to 83.06 g (0.346 mol) of (2£)-3-(3- benzyloxyphenyl)prop-2-en- l -ol (general formula II: R = CH2Ph) preheated in a bath under Ar to 62C, and, after 10 min, tetrabromomethane (5.74 g, 5 mol %) is added. Within 20 min of stirring, a homogeneous solution is formed, which is heated in a bath at 62C for 10 h. The mixture is cooled down, diluted with toluene (420 ml), and washed with a 20% solution of potassium carbonate (200 ml +27 g of solid potassium carbonate). The separated organic phase is then shaken with IN sodium hydroxide (200 ml) for 3 min, washed with water (100 ml) and brine (75 ml), and, after filtration, evaporated in a rotating vacuum evaporator. A crude product is obtained, which is stirred with hexane or petroleum ether ( 125 ml), and optionally inoculated. After 3 h, the crystals are aspirated, washed with the same solvent (75 ml), and dried out freely. 98.04 g (95.7%) of the ester is obtained, melting point = 61 .6 to 62.8C.' H-NMR (CDC13) 5 1 .1 7 (3H, t, J = 7.6 Hz), 2.38 (2H, q, J = 7.6 Hz), 4.73 (2H, d, J =6.4 Hz), 5.07 (2H, s), 6.27 ( 1 H, dt, J = 6.4, 1 5.9 Hz), 6.32 (1 H, d, J = 15.9 Hz), 6.89 ( 1 H, dd, J = 2.5, 8.3 Hz), 6.98-7.01 (2H, m), 7.20-7.39 (6H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With sodium hydride; In tetrahydrofuran; mineral oil; at 20 - 40℃; for 18h;Inert atmosphere; | Sodium hydride (60%, 4.99 g, 125 mmol) was charged to a suitable reactor, and the system was flushed with nitrogen. 100 mL of anhydrous THF was charged to the reactor and agitation was started. <strong>[155697-42-0](E)-3-(3-(benzyloxy)phenyl)prop-2-en-1-ol</strong> (21.3 g, 83.2 mmol) as a solution in 100 mL of THF was charged to the reactor at a rate to maintain the batch temperature between 20 C. and 30 C. Allyl bromide (10.8 mL, 125 mmol) was charged to the reactor. The reaction was agitated at 40 C. for 18 hours. The reaction was diluted with 400 mL of heptane and slowly quenched with 300 mL of water. The layers were separated and the organic portion was washed with 300 mL of water. The organic portion was purified by silica gel chromatography (4% IpAc in heptane) to provide the intended product (E)-1-(3-(allyloxy)prop-1-enyl)-3-(benzyloxy)benzene as a colorless and clear oil (20.7 g, 89% yield). 1H NMR (400 MHz, CDCl3) δ 7.46-7.30 (m, 5H), 7.22 (t, J=7.7 Hz, 1H), 7.09-6.95 (m, 2H), 6.86 (d, J=8.1 Hz, 1H), 6.58 (d, J=15.7 Hz, 1H), 6.28 (ddd, J=6.26, 6.0, 6.0 Hz, 1H), 5.95 (ddd, J=17.3 Hz, 10.6 Hz, 5.71 Hz, 1H), 5.31 (d, J=17.3 Hz, 1H), 5.21 (d, J=10.5 Hz, 1H), 5.06 (s, 2H), 4.15 (d, J=5.96 Hz, 1H), 4.03 (d, J=5.3 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | <strong>[122024-75-3](E)-3-(3-(benzyloxy)phenyl)acrylic acid</strong> (151 g, 594 mmol) was charged to a 2 L jacketed reactor. The reactor was flushed with nitrogen and anhydrous 2-methyltetrahydrofuran (MeTHF, 1.2 L) was charged to the reactor. Agitation was started, and triethylamine (90.0 mL, 646 mmol) was charged to the reactor at a rate to maintain the batch temperature between 10 C. and 20 C. Ethyl chloroformate (60.0 mL, 627 mmol) was charged to the reactor at a rate to maintain the batch temperature between 10 C. and 20 C. The reaction was agitated at 10 C. and 20 C. for 1 hour. Lithium borohydride solution (2.0 M in THF, 290 g, 647 mmol) was charged to the reactor at a rate to maintain the batch temperature between 10 C. and 20 C. The reaction was agitated at 10 C. and 20 C. for 2 hours. 140 mL of water was slowly charged to the reactor at a rate to maintain the batch temperature between 10 C. and 20 C. Aqueous sodium hydroxide (2 M, 480 mL, was slowly charged to the reactor over 30 minutes with a batch temperature between 10 C. and 20 C. 480 mL of water was charged to the reactor. The layers were separated, and the organic portion was washed with 300 mL of water. The organic portion was concentrated in vacuo to 400 mL. 500 mL of ethanol was charged to the reactor and the solution was concentrated in vacuo to 400 mL. This chase was repeated. 150 mL of ethanol was charged to the batch, and the batch temperature was adjusted to 0 C. The solution was seeded to induce crystallization, and the resulting mixture was diluted slowly with 400 mL of water at -5 C. to 0 C. The resulting mixture was agitated for 1 hour at 0 C. The solids were collected by filtration and washed with water. The solids were dried in a vacuum oven with a nitrogen stream at 20 C. to afford the desired (E)-3-(3-(benzyloxy)phenyl)prop-2-en-1-ol as a white solid and the semi-ethanol solvate (114 g, 91 wt %, 4.3 wt % ethanol, 73% yield). 1H NMR (400 MHz, CDCl3) delta 7.46-7.28 (m, 5H), 7.22 (dd, J=8.0, 8.0 Hz, 1H), 7.02-6.96 (m, 2H), 6.86 (d, J=8.0 Hz, 1H), 6.56 (d, J=15.8 Hz, 1H), 6.33 (ddd, J=15.8, 5.6, 5.6 Hz, 1H), 5.05 (s, 2H), 4.29 (d, J=5.6 Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With aluminum oxide; In 1,2-dichloro-ethane; for 6h;Reflux; | General procedure: General Procedure: To a 40 mL reaction vial containing a magnetic stir were added cinnamyl alcohol (134.2 mg, 1.0 mmol), 1 ,2-dichloroethane (10 mL), acidic aluminum oxide (2.0 g), and phenol (141.2 mg, 1.5 mmol). The suspension was stirred and heated at reflux temperature for 24 hours at which point TLC analysis indicated complete consumption of the cinnamyl alcohol substrate. The reaction mixture was cooled and filtered through a pad of Celite. The solids were washed with EtOAc (3 x 30 mL) and the filtrates combined and concentrated in vacuo. Unless otherwise specified, the crude residue was purified via flash column chromatography on silica gel using gradient elution with hexane and ethyl acetate. Compound l-5was isolated as a white solid in 9 % yield (29.3 mg, 0.09 mmol) and Compound MLAP-1909 was isolated as a colorless oil in 73 % yield (153.8 mg, 0.73 mmol). |
Tags: 155697-42-0 synthesis path| 155697-42-0 SDS| 155697-42-0 COA| 155697-42-0 purity| 155697-42-0 application| 155697-42-0 NMR| 155697-42-0 COA| 155697-42-0 structure
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