155697-42-0|3-(3-(Benzyloxy)phenyl)prop-2-en-1-ol| Ambeed

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Quality Control of [ 155697-42-0 ] Purity: 97% SDS Specification

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Product Details of [ 155697-42-0 ]

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

Safety of [ 155697-42-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Application In Synthesis of [ 155697-42-0 ]

* 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.

Downstream synthetic route of [ 155697-42-0 ]

[ 155697-42-0 ] Synthesis Path-Downstream 1~36

1
[ 78-39-7 ]
[ 155697-42-0 ]
[ 155697-43-1 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1817 - 1820.

2
[ 208836-69-5 ]
[ 155697-42-0 ]

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).

References: [1]Patent: WO2012/89181,2012,A1 .Location in patent: Page/Page column 24.
[2]Tetrahedron Letters,1994,vol. 35,p. 1817 - 1820.

3
[ 109-92-2 ]
[ 155697-42-0 ]
[ 208836-70-8 ]

References: [1]Journal of the Indian Chemical Society,1997,vol. 74,p. 864 - 869.

4
[ 63604-98-8 ]
[ 155697-42-0 ]
[ 850307-91-4 ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2177 - 2185.
[2]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2177 - 2185.

5
[ 155697-42-0 ]
4-<(3-phenylmethoxy)phenylmethyl>dihydrofuran-2(3H)-one [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1997,vol. 74,p. 864 - 869.

6
[ 155697-42-0 ]
4-(3-benzyloxy-benzyl)-2-ethoxy-tetrahydro-furan [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1997,vol. 74,p. 864 - 869.

7
[ 1700-37-4 ]
[ 155697-42-0 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1817 - 1820.

8
[ 155697-42-0 ]
3-(3-Benzyloxy-phenyl)-pent-4-en-1-ol [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1817 - 1820.

9
[ 155697-42-0 ]
3-(3-Benzyloxy-phenyl)-4,4-difluoro-butan-1-ol [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1817 - 1820.

10
[ 155697-42-0 ]
[ 155697-44-2 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1817 - 1820.

11
[ 155697-42-0 ]
Acetic acid 3-(3-benzyloxy-phenyl)-4-oxo-butyl ester [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1817 - 1820.

12
[ 155697-42-0 ]
[ 155697-45-3 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1817 - 1820.

13
[ 155697-42-0 ]
[ 155697-46-4 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1817 - 1820.

14
[ 155697-42-0 ]
(+)-3-difluoromethyl-3-(3-benzyloxyphenyl)propionic acid [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1817 - 1820.

15
[ 155697-42-0 ]
(-)-3-difluoromethyl-3-(3-benzyloxyphenyl)propionic acid [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1817 - 1820.

16
[ 155697-42-0 ]
[ 155697-48-6 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1817 - 1820.

17
[ 155697-42-0 ]
[ 155697-47-5 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1817 - 1820.

18
[ 100-39-0 ]
[ 155697-42-0 ]

References: [1]Patent: WO2012/89181,2012,A1 .

19
[ 123-62-6 ]
[ 155697-42-0 ]
[ 1384457-48-0 ]

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).

References: [1]Patent: WO2012/89181,2012,A1 .Location in patent: Page/Page column 23.

20
[ 96251-92-2 ]
[ 155697-42-0 ]

References: [1]Patent: WO2012/89181,2012,A1 .

21
[ 155697-42-0 ]
tapentadol hydrochloride [ No CAS ]

References: [1]Patent: WO2012/89181,2012,A1 .
[2]Patent: US2013/150622,2013,A1 .

22
[ 155697-42-0 ]
[ 1384457-51-5 ]

References: [1]Patent: WO2012/89181,2012,A1 .

23
[ 155697-42-0 ]
[ 1384457-44-6 ]

References: [1]Patent: WO2012/89181,2012,A1 .

24
[ 155697-42-0 ]
[ 1384457-45-7 ]
(2S,3S)-3-(3-benzyloxyphenyl)-2-methylpent-4-enoic acid (R)-1-phenylethylamine salt [ No CAS ]

References: [1]Patent: WO2012/89181,2012,A1 .

25
[ 155697-42-0 ]
(2RS,3RS)-3-(3-benzyloxyphenyl)-2-methylpent-4-enoic acid [ No CAS ]

References: [1]Patent: WO2012/89181,2012,A1 .

26
[ 155697-42-0 ]
[ 1384457-52-6 ]

References: [1]Patent: WO2012/89181,2012,A1 .

27
[ 155697-42-0 ]
[ 1384457-50-4 ]

References: [1]Patent: WO2012/89181,2012,A1 .

28
[ 106-95-6 ]
[ 155697-42-0 ]
[ 1443156-32-8 ]

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).

References: [1]Patent: US2013/150622,2013,A1 .Location in patent: Paragraph 0045; 0046.

29
[ 122024-75-3 ]
[ 155697-42-0 ]

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).

References: [1]Patent: US2013/150622,2013,A1 .Location in patent: Paragraph 0043; 0044.

30
[ 155697-42-0 ]
[ 175591-23-8 ]

References: [1]Patent: US2013/150622,2013,A1 .

31
[ 155697-42-0 ]
[ 1443156-34-0 ]

References: [1]Patent: US2013/150622,2013,A1 .

32
[ 155697-42-0 ]
[ 1367878-83-8 ]

References: [1]Patent: US2013/150622,2013,A1 .

33
[ 155697-42-0 ]
[ 1443156-35-1 ]

References: [1]Patent: US2013/150622,2013,A1 .

34
[ 155697-42-0 ]
1-(benzyloxy)-3-((E)-3-((E)-prop-1-enyloxy)prop-1-enyl)benzene [ No CAS ]

References: [1]Patent: US2013/150622,2013,A1 .

35
[ 1026884-98-9 ]
[ 155697-42-0 ]

References: [1]Patent: US2013/150622,2013,A1 .

36
[ 14755-02-3 ]
[ 155697-42-0 ]

References: [1]Patent: US2013/150622,2013,A1 .

Historical Records

Technical Information

• Appel Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Hydride Reductions • Jones Oxidation • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Nomenclature of Ethers • Oxidation of Alcohols by DMSO • Preparation of Alcohols • Preparation of Amines • Preparation of Ethers • Reactions of Alcohols • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Swern Oxidation

Related Functional Groups of
[ 155697-42-0 ]

Aryls

A635587 [89946-06-5]

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Alkenyls

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Ethers

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H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 155697-42-0

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