[ CAS No. 56718-71-9 ] {[proInfo.proName]}

Name: 56718-71-9|p-(2-Methoxyethyl) phenol|97%
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Quality Control of [ 56718-71-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 56718-71-9 ]

SDS Specification

Alternatived Products of [ 56718-71-9 ]

Product Details of [ 56718-71-9 ]

CAS No. :	56718-71-9	MDL No. :	MFCD00017537
Formula :	C₉H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FAYGEALAEQKPDI-UHFFFAOYSA-N
M.W :	152.19	Pubchem ID :	92516
Synonyms :	p-Hydroxyphenethyl methyl ether	Chemical Name :	p-(2-Methoxyethyl) phenol

Calculated chemistry of [ 56718-71-9 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	44.13
TPSA :	29.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.91
Log Po/w (XLOGP3) :	1.9
Log Po/w (WLOGP) :	1.58
Log Po/w (MLOGP) :	1.53
Log Po/w (SILICOS-IT) :	2.0
Consensus Log Po/w :	1.78

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.19
Solubility :	0.991 mg/ml ; 0.00651 mol/l
Class :	Soluble
Log S (Ali) :	-2.14
Solubility :	1.1 mg/ml ; 0.00722 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.74
Solubility :	0.276 mg/ml ; 0.00181 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.07

Safety of [ 56718-71-9 ]

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:

Application In Synthesis of [ 56718-71-9 ]

* 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.

Upstream synthesis route of [ 56718-71-9 ]
Downstream synthetic route of [ 56718-71-9 ]

[ 56718-71-9 ] Synthesis Path-Upstream 1~1

1
[ 56718-71-9 ]
[ 51384-51-1 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 5, p. 738 - 747
[2] Chemical Communications, 2015, vol. 51, # 82, p. 15133 - 15136
[3] Catalysis Science and Technology, 2014, vol. 4, # 11, p. 3899 - 3908
[4] Patent: WO2005/46568, 2005, A2,

[ 56718-71-9 ] Synthesis Path-Downstream 1~88

1
[ 14140-15-9 ]
[ 124-41-4 ]
[ 56718-71-9 ]

Reference： [1]Russian Journal of General Chemistry,2010,vol. 80,p. 275 - 283
[2]Journal of the American Chemical Society,1957,vol. 79,p. 756

2
[ 56718-71-9 ]
[ 67589-90-6 ]
4-Pentyl-cyclohexanecarboxylic acid 4-(2-methoxy-ethyl)-phenyl ester [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1985,vol. 130,p. 231 - 248
[2]Molecular Crystals and Liquid Crystals (1969-1991),1984,vol. 112,p. 319 - 324

3
[ 56718-71-9 ]
[ 67589-92-8 ]
4-Heptyl-cyclohexanecarboxylic acid 4-(2-methoxy-ethyl)-phenyl ester [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1985,vol. 130,p. 231 - 248

4
[ 56718-71-9 ]
2,5-O-methylene-3,4-O-methoxymethylene-1,6-di-O-p-toluenesulfonyl-D-mannitol [ No CAS ]
[ 114218-32-5 ]

Reference： [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1987,vol. 41,p. 202 - 207

5
[ 84803-56-5 ]
[ 56718-71-9 ]

Reference： [1]Synthetic Communications,1985,vol. 15,p. 1131 - 1136

6
[ 32136-81-5 ]
[ 56718-71-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With hydrogen; under 3000.3 Torr;Heating;	steps 2 taken to generate the reaction of 4-(2'-methoxyacetyl) phenol) was added to the reaction vessel, 5g of Raney nickel catalyst, introducing hydrogen as a reducing agent, open stirring, heating, the hydrogen pressure is controlled 0.4 MPa, reaction of intermediate 4-(2'-methoxyethyl)phenol.
0.54 g (3.6 mmol=61%)	With H2; acetic acid;palladium-carbon;	EXAMPLE 5 Hydrogenation of <strong>[32136-81-5]alpha-methoxy-4-hydroxyacetophenone</strong>: A 300 ml Fluitron autoclave (Hastelloy C) is charged with 1 g <strong>[32136-81-5]alpha-methoxy-4-hydroxyacetophenone</strong> (95.9%, 5.8 mmol), 80 ml acetic acid and 0.3 g Pd/C (5% Pd on carbon; 47.8% H2 O). After sealing, the stirrer is started, and the autoclave purged with nitrogen and hydrogen and finally pressurized to 250 psig H2. After reaching the reaction temperature of 80 C., the H2 pressure is kept constant at 300 psig over the 2 hour reaction period. The autoclave is vented and purged with N2. The reaction mixture is removed from the reactor, filtered and finally analyzed by GC, using independently made 4-(2'-methoxyethyl)phenol as an external standard. Yield: 0.54 g (3.6 mmol=61%) 4-(2'-methoxyethyl)phenol, 0.23 g (1.5 mmol=25%) 4-(2'-methoxyethyl)cyclohexanol (estimation, using the GC response factor of 4-(2'-methoxyethyl)phenol)

Reference： [1]Synthetic Communications,1990,vol. 20,p. 3489 - 3496
[2]Patent: CN107382683,2017,A .Location in patent: Paragraph 0012; 0013; 0014
[3]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 191 - 194
[4]Patent: US5107034,1992,A

7
[ 98627-35-1 ]
[ 56718-71-9 ]

Yield	Reaction Conditions	Operation in experiment
38.6 g	With palladium 10% on activated carbon; hydrogen; under 37503.8 Torr; for 3h;	Add 68.8g of p-benzyloxyphenylethanol to a 1000mL three-necked flask,20.9 g of sodium hydroxide, 220 g of toluene,Stir the mixture to reflux with water, bring water for 2h,Add 39.79g of dimethyl sulfate dropwise and add the reaction for 2h.Cool to room temperature, filter, add to the toluene solution of p-benzyloxyphenethyl methyl ether7g of 10% palladium carbon, pressurized to 5MPa, reacted for 3h, filtered,Concentrated to recover toluene,Obtaining crude p-methoxyethylphenol,Rectification gave 38.6 g of p-methoxyethylphenol with a purity of > 99%.

Reference： [1]Food Chemistry,2011,vol. 129,p. 1169 - 1178
[2]Tetrahedron,1985,vol. 41,p. 1367 - 1372
[3]Patent: CN108689810,2018,A .Location in patent: Paragraph 0037-0038

8
[ 56718-71-9 ]
[ 106-95-6 ]
[ 80448-05-1 ]

Reference： [1]Letters in Organic Chemistry,2012,vol. 9,p. 516 - 519
[2]Synthetic Communications,1990,vol. 20,p. 3489 - 3496

9
[ 82099-82-9 ]
[ 56718-71-9 ]

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1985,vol. 130,p. 231 - 248
[2]Molecular Crystals and Liquid Crystals (1969-1991),1984,vol. 112,p. 319 - 324

10
[ 56718-71-9 ]
[ 135-19-3 ]
[ 89391-37-7 ]

Reference： [1]Tetrahedron,1985,vol. 41,p. 1367 - 1372

11
[ 56718-71-9 ]
[ 76-04-0 ]
α,α-difluoro[4-(2-methoxyethyl)phenoxy]acetic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1273 - 1274

12
[ 56718-71-9 ]
[ 107-21-1 ]
4-(2-hydroxy-ethoxy)-4-(2-methoxy-ethyl)-cyclohexa-2,5-dienone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With [bis(acetoxy)iodo]benzene; In dichloromethane; at 20℃; for 2.5h;Inert atmosphere;	General procedure: A flame-dried 100 ml round bottom flask was charged with phenol I (1.08 g, 10mmol); the flask was purged under vacuum for 5 mins and then refilled with argonand 2 ml CH2Cl2. Ethylene glycol (16.7 ml, 300 mmol) and then PhI(OAc)2 (4.83g, 15 mmol, dissolved in 40 ml CH2Cl2) was added dropwise over 2 hours. Thes olution was then allowed to stir at ambient temperature for further 30 mins. The solution was concentrated in vacuo and the residue was subjected to column chromatography (EtOAc : Hexane = 1:1).

Reference： [1]Organic Process Research and Development,2007,vol. 11,p. 598 - 604
[2]Journal of the American Chemical Society,2006,vol. 128,p. 2552 - 2553
[3]Synlett,2016,vol. 27,p. 1602 - 1606

13
[ 56718-71-9 ]
2-iodo-4-(2-methoxy-ethyl)-phenol [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 81 - 83

14
[ 56718-71-9 ]
[ 140645-28-9 ]
[ 935547-68-5 ]

Reference： [1]Chemistry and Physics of Lipids,2006,vol. 144,p. 69 - 84
[2]Synthetic Communications,2007,vol. 37,p. 2737 - 2751
[3]European Journal of Organic Chemistry,2008,p. 150 - 155

15
C₁₉H₂₈N₂O₃ [ No CAS ]
[ 56718-71-9 ]
C₂₃H₃₂N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		SYNTHETIC EXAMPLE 2 SCHEME 3 A preparation of Compound (XXXI) is depicted in Scheme 3. In one approach, 4- (2-methoxyethyl)phenol may react with epichlorohydrin (ECH) to form epoxide 16 using the same conditions as described for Compound (XXX). Nucleophilic displacement of the leaving group of 14 with an excess 3-(R)-(t- butyloxycarbonyl) aminopyrrolidine (about 3-7 equivalents) at a suitable temperature (e. g. about 60-70C) for an appropriate reaction time period (e. g. about 4-18 h) may provide 15. Hydrolysis of the carbamate group of 15 in ethereal HCI followed by neutralization and condensation with 16 in refluxing acetonitrile may give Compound (XXXI). However, an alternative preferred synthetic pathway as shown in Scheme 3 may be mono N-benzylation of N-boc-3- (R)-aminopyrrolidine reductive amination (Panfilov, A. V. ; Markovich, Yu. D. ; Zhirov, A. A.; Ivashev, I. P. ; Kirsanov, A. T.; Kondrat'ev, V. B. Reactions of Sodium Borohydride in Acetic Acid: Reductive Amination of Carbonyl Compounds Pharm.Chem.J. (EngLTransl.) (7), 371 - 373) followed by N.-alkylation with allyl bromide in the presence of NaOH aqueous in EtOH. Subsequent epoxidation with m-chloroperbenzoic acid (Gregorio Asensio, Rossella Mello, Carmen Boix-Bernardini, Maria Elena Gonzlez-Nunez, and Gloria Castellano Epoxidation of primary and Secondary Alkenylammonium Salts with Dimethyloxirane, Methyl(trifluoromethyl)dioxirane, and m-Chloroperbenzoic Acid. A General Synthetic Route to Epoxyalkylamines. J. Org. Chem. 1995,60, 3692-3699) or as reported by Hou et al. (for example: Esmolol, Acebutolol, Practolol, Atenolol, Celiprolol, Betaxolol, Cetamolol, Bisoprolol and Bevantolol may provide epoxide 8. The epoxide 8 may be reacted as previously described with 4- (2-methoxyethyl)phenol the presence of NaOH aqueous in EtOH. Hydrolysis of the carbamate group in ethereal HCI may be followed by neutralization and the resultant free aminoalcohol 9 may displace the leaving group (e. g. nosylate, ONs) of 14 to give, after debenzylation, Compound (XXXI).

Reference： [1]Patent: WO2005/97087,2005,A2 .Location in patent: Page/Page column 75, 76

16
[ 56718-71-9 ]
[ 88285-82-9 ]
C₂₆H₃₁NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol; water;	SYNTHETIC EXAMPLE 4 SCHEME 5 Compound (XXXII) may be prepared from 14 and 4- (2-methoxyethyl)phenol depicted in Scheme 5. Ring epoxide opening of 16 with NH40H may give aminoalcohol 17, which then may react with 14 to yield Compound (XXXII). However, an alternative synthetic pathway may comprise preparing N,N-dibenzyl-2,3-epoxypropylamine according to Bakalarz-Jeziorna et al. (Agata Bakalarz-Jeziorna, Jan Helinski and Bozena Krawiecka Synthesis of multifunctionalized phosphonic acid esters via opening of oxiranes and azetidium salts with phosphoryl-substituted carbanions. J. Chem. Soc. , Perkin Trans. 1, 2001, 1086-1090). Epoxide opening with <strong>[56718-71-9]4-(2-methoxyethyl)phenol</strong> may give 18. 18 may then be N-debenzylated and followed by reaction with 14 to provide Compound (XXXII).

Reference： [1]Patent: WO2005/97087,2005,A2 .Location in patent: Page/Page column 77, 78

17
[ 56718-71-9 ]
[ 952196-64-4 ]

Reference： [1]Synthetic Communications,2007,vol. 37,p. 2737 - 2751

18
[ 56718-71-9 ]
[ 952196-66-6 ]

Reference： [1]Synthetic Communications,2007,vol. 37,p. 2737 - 2751

19
[ 56718-71-9 ]
(R)-2-amino-3-[4-(2-methoxyethyl)phenoxy]propyl dihydrogenphosphate [ No CAS ]

Reference： [1]Synthetic Communications,2007,vol. 37,p. 2737 - 2751

20
[ 56718-71-9 ]
[ 881181-57-3 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 2552 - 2553
[2]Synlett,2016,vol. 27,p. 1602 - 1606

21
[ 56718-71-9 ]
[ 691841-17-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3532 - 3535

22
[ 56718-71-9 ]
2-(benzyl-{2-hydroxy-3-[4-(2-methoxy-ethyl)-phenoxy]-propyl}-amino)-1-(4-benzyloxy-phenyl)-propan-1-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3532 - 3535

23
[ 56718-71-9 ]
[ 56718-76-4 ]

Reference： [1]Synthetic Communications,2005,vol. 35,p. 2195 - 2201
[2]RSC Advances,2017,vol. 7,p. 36566 - 36574

24
[ 2491-38-5 ]
[ 56718-71-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 191 - 194

25
[ 56718-71-9 ]
(R)-2-{(R)-2-Hydroxy-3-[4-(2-methoxy-ethyl)-phenoxy]-propylamino}-butan-1-ol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 191 - 194

26
[ 56718-71-9 ]
(2S)-2-[[(2R)-2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl]amino]-1-butanol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 191 - 194

27
[ 56718-71-9 ]
(R)-2-{(S)-2-Hydroxy-3-[4-(2-methoxy-ethyl)-phenoxy]-propylamino}-butan-1-ol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 191 - 194

28
[ 56718-71-9 ]
(2S)-2-[[(2S)-2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl]amino]-1-butanol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 191 - 194

29
[ 99-93-4 ]
[ 56718-71-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 191 - 194

30
[ 56718-71-9 ]
[ 185758-10-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1273 - 1274

31
[ 56718-71-9 ]
(R)-1,1-difluoro-1-[4-(2-methoxyethyl)phenyl]oxy-3-nitropropan-2-ol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1273 - 1274

32
[ 56718-71-9 ]
[ 192575-81-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1273 - 1274

33
[ 56718-71-9 ]
[ 192575-80-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1273 - 1274

34
[ 56718-71-9 ]
(R)-1,1-Difluoro-3-isopropylamino-1-[4-(2-methoxy-ethyl)-phenoxy]-propan-2-ol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1273 - 1274

35
[ 56718-71-9 ]
(S)-1,1-Difluoro-3-isopropylamino-1-[4-(2-methoxy-ethyl)-phenoxy]-propan-2-ol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1273 - 1274

36
[ 56718-71-9 ]
[ 51384-51-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 738 - 747
[2]Chemical Communications,2015,vol. 51,p. 15133 - 15136
[3]Catalysis science and technology,2014,vol. 4,p. 3899 - 3908
[4]Patent: WO2005/46568,2005,A2

37
[ 56718-71-9 ]
N-isopropyl-3-<<4'-(2''-methoxyethyl)phenyl>oxy>-2-oxo-1-propylamine [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 738 - 747

38
[ 60-12-8 ]
ZnCl₂ [ No CAS ]
[ 56718-71-9 ]

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1984,vol. 112,p. 319 - 324
[2]Molecular Crystals and Liquid Crystals (1969-1991),1985,vol. 130,p. 231 - 248

39
[ 99215-51-7 ]
[ 56718-71-9 ]

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1984,vol. 112,p. 319 - 324
[2]Molecular Crystals and Liquid Crystals (1969-1991),1985,vol. 130,p. 231 - 248

40
[ 93205-89-1 ]
[ 56718-71-9 ]

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1984,vol. 112,p. 319 - 324
[2]Molecular Crystals and Liquid Crystals (1969-1991),1985,vol. 130,p. 231 - 248

41
[ 56718-71-9 ]
[ 111794-55-9 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 345 - 351

42
[ 56718-71-9 ]
[ 111794-29-7 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 345 - 351

43
[ 73823-79-7 ]
[ 56718-71-9 ]

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1985,vol. 130,p. 231 - 248

44
[ 103-45-7 ]
[ 56718-71-9 ]

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1985,vol. 130,p. 231 - 248

45
[ 586-78-7 ]
magnesium [ No CAS ]
[ 56718-71-9 ]

Reference： [1]Synthetic Communications,1985,vol. 15,p. 1131 - 1136

46
[ 56718-71-9 ]
[ 104450-89-7 ]

Reference： [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1987,vol. 41,p. 202 - 207

47
[ 56718-71-9 ]
[ 104450-87-5 ]

Reference： [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1987,vol. 41,p. 202 - 207

48
[ 56718-71-9 ]
[ 104450-88-6 ]

Reference： [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1987,vol. 41,p. 202 - 207

49
[ 56718-71-9 ]
[ 104450-91-1 ]

Reference： [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1987,vol. 41,p. 202 - 207

50
[ 56718-71-9 ]
[ 104450-90-0 ]

Reference： [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1987,vol. 41,p. 202 - 207

51
[ 501-94-0 ]
[ 56718-71-9 ]

Yield	Reaction Conditions	Operation in experiment
40%	With sulfuric acid; In methanol;	EXAMPLE 1 4-(2'-Methoxyethyl)Phenol A solution of twenty (20) grams 4-hydroxyphenethyl alcohol in 150 ml methanol containing 36.75 grams sulfuric acid (catalyst) were loaded into a 300 cc autoclave. The autoclave was then sealed and purged with nitrogen and pressurized with nitrogen gas to 500 psig. The autoclave was then heated to 100 C. with stirring at 300 rpm. The reaction was allowed to take place for approximately twenty-four (24) hours. The autoclave was then purged with nitrogen, cooled to 5 C., and vented slowly. The resultant material was 90 ml of a dark, greenish-black solution. An aliquot was treated with base and analyzed by gas chromatography (GC). A 40% yield of 4-(2'-methoxyethyl)phenol was obtained.
31%	In methanol;	Example 3 4-(2'-Methoxyethyl)Phenol A mixture of 20.0 grams 4-hydroxyphenethyl alcohol, 100 ml methanol, and 10.0 grams Dowex 50 (H+form) catalyst were loaded into an autoclave. The autoclave was then sealed and purged with nitrogen and pressurized with nitrogen gas to 200 psig. The autoclave was then vented of excess pressure, sealed, and heated to 118 C. over a sixteen (16) hour period with stirring at 300 rpm. The pressure rose from 200 psig to 440 psig. The reaction was allowed to take place for approximately sixteen (16) hours. The autoclave was then purged with nitrogen and cooled to 17.2 C. (230 psig) and then vented. The solid catalyst was filtered off, providing 15.5 grams of oil which solidified. A 31% yield of 4-(2'-methoxy-ethyl)phenol was obtained.
	With nitrogen; In methanol; water;	Example 11 4-(2'-Methoxyethyl) Phenol A mixture of 4-hydroxyphenethyl alcohol (60 grams, 0.435 moles), methanol (18 ml), water (26 ml), and a ZSM-5 Zeolite (UOP MFI-38 or MFI-34, 10 grams) are charged to a 300 cc autoclave. The alcohols and water are not a homogenous solution at room temperature. The reactor is charged with 200 psig of nitrogen and is then heated with stirring to 150 C. for 17 hours. Pressure maximizes at about 350 psig. The reactor is then cooled and vented. The product is then purged with nitrogen and filtered. The methanol is removed on a rotary evaporator. The product is isolated by distillation. The conversion to 4-(2'-methoxyethyl) phenol is about 50%.

Reference： [1]Patent: US5602285,1997,A
[2]Patent: US5602285,1997,A
[3]Tetrahedron,1985,vol. 41,p. 1367 - 1372
[4]Patent: US5602285,1997,A
[5]Food Chemistry,2011,vol. 129,p. 1169 - 1178
[6]Tetrahedron Letters,2013,vol. 54,p. 5004 - 5006

52
[ 61439-59-6 ]
[ 56718-71-9 ]

Reference： [1]Tetrahedron,1985,vol. 41,p. 1367 - 1372
[2]Food Chemistry,2011,vol. 129,p. 1169 - 1178

53
[ 6305-04-0 ]
[ 56718-71-9 ]

Reference： [1]Synthetic Communications,1990,vol. 20,p. 3489 - 3496

54
[ 56718-71-9 ]
[ 62572-90-1 ]

Reference： [1]Synthetic Communications,1990,vol. 20,p. 3489 - 3496

55
[ 56718-71-9 ]
[ 74254-83-4 ]

Reference： [1]Synthetic Communications,1990,vol. 20,p. 3489 - 3496

56
[ 56718-71-9 ]
[ 56718-70-8 ]

Reference： [1]Synthetic Communications,1990,vol. 20,p. 3489 - 3496

57
[ 108-95-2 ]
[ 56718-71-9 ]

Reference： [1]Synthetic Communications,1990,vol. 20,p. 3489 - 3496
[2]Patent: CN107382683,2017,A

58
[ 56718-71-9 ]
[ 115314-14-2 ]
[ 105780-38-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; In butanone; for 18h;Heating / reflux;	2-[4-(2-Methoxy-ethyl)-phenoxymethyll-oxirane (3r); To a stirred solution of <strong>[56718-71-9]4-(2-methoxy-ethyl)-phenol</strong> ((1r), 200 mg, 1.31 mmol) and 3-nitro-benzenesulfonic acid oxiranylmethyl ester ((2), 342 mg, 1.31 mmol) in butan-2-one was added potassium carbonate (200 mg, 1.45 mmol). The mixture was stirred under reflux for 18 h and the solvent then removed under reduced pressure. The residue was separated between dichloromethane (25 ml_) and water (25 ml_). The aqueous phase was extracted with dichloromethane (2 * 25 ml_). The combined organic layers were washed with aqueous sodium hydroxide solution (2/V, 25 ml_) and saturated brine (25 ml_), dried over sodium sulphate and evaporated to dryness to give 2-[4-(2-methoxy-ethyl)-phenoxymethyl]-oxirane (3r) as a yellow oil (250 mg, 92% yield, 95% pure by LC-MS and 1H-nmr).

Reference： [1]Patent: WO2006/60122,2006,A2 .Location in patent: Page/Page column 80

59
[ 4285-42-1 ]
[ 56718-71-9 ]
[ 548765-61-3 ]

Yield	Reaction Conditions	Operation in experiment
		Methyl-phenyl-carbamic Acid 4-(2-methoxy-ethyl)-phenyl Ester The title product was prepared from <strong>[56718-71-9]4-(2-methoxyethyl)phenol</strong> and N-methyl-N-phenylcarbamoyl chloride. The crude product was subjected to preparative HPLC. (4%, light yellow oil). HPLC-MS: m/z=286.1 (M+1); Rt: 4.01 min. 1H NMR (CDCl3): 7.30-7.48 (m, 4H), 7.12-7.30 (m, 3H), 7.03 (d, 2H), 3.56 (t, 2H), 3.42 (s, 3H), 3.33 (s, 3H), 2.85 (t, 2H).

Reference： [1]Patent: US2003/166644,2003,A1

60
[ 501-94-0 ]
[ 144-55-8 ]
[ 56718-71-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	In methanol;	Example 9 4-(2'Methoxyethyl)Phenol A mixture of 80 grams of 4-hydroxyphenethyl alcohol (0.58 moles), methanol (100 ml), and 10 grams of Dowex 50 catalyst (H30 form, washed with methanol) was charged into a 300 cc autoclave. The autoclave was sealed, purged with nitrogen and then pressurized under nitrogen. The autoclave was heated to 150 C. overnight with stirring (about 16 hours). The reactor was then cooled, depressurized, and purged with nitrogen to remove by-product dimethyl ether. The catalyst was filtered off and a few drops of saturated aqueous sodium bicarbonate solution were added to neutralize acidity. The solvent was removed on a rotary evaporator. The product was isolated in 65% yield by distillation, with 33% of the 4-hydroxyphenethyl alcohol remaining unreacted.

Reference： [1]Patent: US5602285,1997,A

61
[ 56718-71-9 ]
[ 106-89-8 ]
3-4-(2-methoxyethyl)phenoxy1-1,2-epoxypropane [ No CAS ]
[ 96-24-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In water;	EXAMPLE 1 To obtain 3-4-(2-methoxyethyl)phenoxy1-1,2-epoxypropane. 25 kg of previously melted <strong>[56718-71-9]4-(2-methoxyethyl)phenol</strong> are added to a solution of 7.4 kg of sodium hydroxide in 160 1 of water, maintaining the temperature between 10 and 15 C. 30 kg of epichlorohydrin are added to the suspension of sodium phenolate at the said temperature. The mixture is stirred for about 15-20 hours at 20-25 C. The organic phase is decanted and washed twice with 25 1 of water. The aqueous extracts are dried, and the excess epichlorohydrin is distilled from the organic phase, 31.5 kg (92%) of a slightly yellowish liquid which contains 75-80% epoxide and 15-20% of the chlorohydrin being obtained in this manner.

Reference： [1]Patent: US5082969,1992,A

62
4-hydroxyphenyl glyoxal dimethylacetal [ No CAS ]
[ 56718-71-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	palladium-carbon; In hydrogenchloride; methanol;	EXAMPLE 2 4-(2'-Methoxyethyl)phenol A solution of 1.00 g (5.1 mmol) 4-hydroxyphenylglyoxal dimethyl acetal in 10 g methanol containing 0.19 g (5.1 mmol) hydrogen chloride and a 0.05 g moist 10% Pd/C catalyst were loaded into an autoclave. The autoclave was then sealed and purged with nitrogen and pressurized with hydrogen gas to 300 psig. The autoclave was then heated up to 50 C. with stirring at 800 rpm. The reaction was allowed to take place for approximately two (2) hours. The autoclave was then purged with nitrogen and cooled to room temperature. The catalyst was filtered off providing a clear filtrate A 70% yield of 4-(2'-methoxyethyl)phenol was obtained
59%	With hydrogen;palladium-carbon; In hydrogenchloride; methanol;	EXAMPLE 4 4-(2'-Methoxyethyl)phenol The procedure of Example 2 was repeated with a solution of 3.00 g (15.3 mmol) 4-hydroxyphenylglyoxal dimethyl acetal in 10 g methanol containing 0.16 g (4.4 mmol) hydrogen chloride and 0.15 g moist 10% Pd/C catalyst being reacted with hydrogen gas pressurized at 300 psig at 50 C. 300 rpm. A 59% yield of 4-(2'-methoxyethyl)phenol was obtained.
53%	With hydrogen;palladium-carbon; In methanol;	EXAMPLE 3 4-(2'-Methoxyethyl)phenol The procedure of Example 2 was repeated with a solution of 2.00 g (10.2 mmol) 4-hydroxyphenylglyoxal dimethyl acetal in 10 g methanol containing 0.23 g (6.3) mmol) hydrogen chloride and 0.20 g moist 10% Pd/C catalyst being reacted with hydrogen ga pressurized at 170 psig at 25 C. with stirring of 550 rpm. A 53% yield of 4-(2'-methoxyethyl)phenol was obtained.

47%

With hydrogenchloride; hydrogen;palladium-carbon; In methanol;

EXAMPLE 5 4-(2'-Methoxyethyl)phenol The procedure of Example 2 was repeated with a solution of 2.00 g (10.2) mmol) 4-hydroxyphenylglyoxal dimethyl acetal in 10 g methanol containing 0.37 g (10.2 mmol) hydrogen chloride and a 0.20 g dry 10% Pd/C catalyst being reacted with hydrogen gas pressurized at 50 psig at 25 C. A 47% yield of 4-(2'-methoxyethyl)phenol was obtained.

Reference： [1]Patent: US5124489,1992,A
[2]Patent: US5124489,1992,A
[3]Patent: US5124489,1992,A
[4]Patent: US5124489,1992,A

63
[ 7790-28-5 ]
[ 56718-71-9 ]
[ 23616-79-7 ]
[ 87130-01-6 ]

Yield	Reaction Conditions	Operation in experiment
	With boric acid; In ethanol; chloroform; water;	EXAMPLE 16 4-(2-Methoxy-ethyl)-phenoxy-acetaldehyde 39 g of <strong>[56718-71-9]4-(2-methoxy-ethyl)-phenol</strong> are heated to about 120 C., after addition of 0.5 g of benzyl-tributylammonium chloride, and 20.4 g of 2,3-epoxypropanyl are added dropwise in the course of 15 minutes. The mixture is allowed to cool, the syrup is dissolved in CHCl3, the solution is washed with water and the CHCl3 residue is purified by preparative HPLC. 50 g of 3-[4-(2-methoxyethyl-phenoxy]-propane-1,2-diol are obtained. Melting point: about 25 C. A solution of 2.5 g of sodium meta-periodate in 100 ml of water and 13 ml of 0.1N boric acid is added dropwise to 12 g of the above diol in 100 ml of ethanol at 10-15 C. After one hour, the NaIO3 is filtered off, the filtrate is diluted with water and the aldehyde is extracted with CHCl3. After the solvent has been evaporated off, 11 g of 4-(2-methoxy-ethyl)-phenoxyacetaldehyde remain as the mono-ethyl acetal. Melting point of the 2,4-dinitrophenylhydrazone: 106-108 C.

Reference： [1]Patent: US4864061,1989,A

64
[ 56718-71-9 ]
[ 113826-06-5 ]
[ 105780-38-9 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; mineral oil;	EXAMPLE 16 Preparation of (2S)-2-[4-(2-Methoxyethyl)phenoxy]methyl}oxirane To a solution of 4-(2-methoxyethyl)phenol (42 mg, 0.275 mmol) and (2S)-(+)-glycidyl tosylate (57 mg, 0.25 mmol) in 2 mL of DMF was added 15 mg (0.625 mmol) of sodium hydride (60% in mineral oil). The resulting mixture was allowed to stir for 16 hours at room temperature. The solution was then extracted three times with ethyl acetate, and the organic phase was washed sequentially with sodium hydroxide, water and brine, dried over sodium sulfate, and concentrated in vacuo to provide the product which was used without further purification. m/z 208 [M+H]+.

Reference： [1]Patent: US2003/78258,2003,A1

65
[ 56718-71-9 ]
[ 171818-94-3 ]
C₂₁H₃₃NO₆ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2008,p. 150 - 155

66
[ 13831-03-3 ]
[ 56718-71-9 ]
(Z)-tert-butyl-3-(4-(2-methoxyethyl)phenoxy)acrylate [ No CAS ]
(E)-tert-butyl-3-(4-(2-methoxyethyl)phenoxy)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; In dichloromethane; at 20℃; for 24h;	a mixture of 4-(2-methoxy ethyl) phenol (1.547g, 10.3 mmol), propiolic acid tert-butyl ester (1.367g, 10.8 mmol) and N-methyl morpholine (1.18 mL, 10.8 mmol) in CH2Cl2 (15 mL) was stirred at room temperature for 24 hours. The mixture was absorbed on SiO2 (20 g) and purified by column chromatography using a mixture of methylene chloride/hexane. The product was obtained as a two to one mixture of (E)/ (Z)-tert-butyl 3-(4-(2-methoxyethyl)phenoxy)acrylate isomers (2.0 g).
	With 4-methyl-morpholine; In dichloromethane; at 20℃; for 24h;	CH2Cl2 (15 mL) solution of 4- (2-methoxyethyl) phenol (1.547g, 10.3mmol), propiolic acid tert- butyl ester (1.367g, 10.8mmol) and N- methylmorpholine (1 .18mL,10.8mmol) and the mixture was stirred for 24 hours at room temperature. Mixture is absorbed on SiO2 (20 g), it was purified by column chromatography using a mixture of methylene chloride / hexane. The product was obtained as a mixture of 2-one (E) / (Z) -tert- butyl 3- (4- (2-methoxyethyl) phenoxy) acrylate isomers (2.0 g). It was obtained as a mixture of 2:1.
	With 4-methyl-morpholine; In dichloromethane; at 20℃; for 24h;	Example 1D3: Preparation of 3-(4-(2-methoxyethyl)phenoxy)propanoic acid; Step 1 : a mixture of 4-(2-methoxy ethyl) phenol (1.547g, 10.3 mmol), propiolic acid tert-butyl ester (1.367g, 10.8 mmol) and N-methyl morpholine (1.18 mL, 10.8 mmol) in CH2Cl2 (15 mL) was stirred at room temperature for 24 hours. The mixture was absorbed on SiO2 (20 g) and purified by column chromatography using a mixture of methylene chloride/hexane. The product was obtained as a two to one mixture of (E)/ (Z)-tert-butyl 3-(4-(2-methoxyethyl)phenoxy)acrylate isomers (2-0 g).

Reference： [1]Patent: WO2010/39256,2010,A1 .Location in patent: Page/Page column 92
[2]Patent: JP2016/41761,2016,A .Location in patent: Paragraph 0186
[3]Patent: WO2008/150486,2008,A2 .Location in patent: Page/Page column 92

67
[ 56718-71-9 ]
[ 106-89-8 ]
[ 56718-76-4 ]

Reference： [1]Tetrahedron Asymmetry,2008,vol. 19,p. 2439 - 2442

68
[ 733747-96-1 ]
[ 56718-71-9 ]
[ 733748-32-8 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 5172 - 5175

69
[ 56718-71-9 ]
[ 627-18-9 ]
[ 1153248-37-3 ]

Yield	Reaction Conditions	Operation in experiment
	With water; potassium carbonate; In acetonitrile; for 3h;Heating / reflux;	Compound (7-2-1): 3-[4-(2-Methoxyethyl)phenoxy]propan-1-ol A solution of <strong>[56718-71-9]4-(2-Methoxyethyl)phenol</strong> (1.00 g, 6.57 mmol), 3-Bromo-1-propanol (771 muL, 8.54 mmol), potassium carbonate (2.00 g, 14.5 mmol), and water (200 muL) in acetonitrile (20 mL) was heated under reflux for 3 hours. After cooling to room temperature, the salt was separated by filtration. The filtrate was concentrated under reduced pressure. The obtained concentrated residue was separated into aqueous and organic layers by the addition of water (5 mL) and toluene (5 mL). The aqueous layer was extracted with toluene (5 mL*2). The combined organic layers were washed with a 0.5 N aqueous sodium hydroxide solution (2 mL) and 1% potassium bisulfate (2 mL) and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure to obtain the title compound (7-2-1) (1.56 g).

Reference： [1]Patent: US2010/113792,2010,A1 .Location in patent: Page/Page column 24

70
[ 5731-01-1 ]
[ 56718-71-9 ]
C₂₃H₂₂O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5872 - 5876

71
[ 56718-71-9 ]
[ 107-30-2 ]
[ 1307311-57-4 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 4972 - 4975

72
[ 56718-71-9 ]
[ 1339949-16-4 ]
[ 113798-79-1 ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 5355 - 5358

73
[ 67843-74-7 ]
[ 56718-71-9 ]
[ 105780-38-9 ]
[ 133397-54-3 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 8768 - 8780

74
[ 51594-55-9 ]
[ 56718-71-9 ]
[ 105780-38-9 ]
[ 133397-54-3 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 8768 - 8780

75
[ 56718-71-9 ]
[ 81024-43-3 ]
[ 81024-42-2 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 8768 - 8780
[2]Journal of Organic Chemistry,2011,vol. 76,p. 8768 - 8780
[3]Journal of Organic Chemistry,2011,vol. 76,p. 8768 - 8780
[4]Journal of Organic Chemistry,2011,vol. 76,p. 8768 - 8780

76
[ 240408-80-4 ]
[ 56718-71-9 ]
[ 1333949-81-7 ]

Reference： [1]Organic Process Research and Development,2011,vol. 15,p. 1365 - 1370

77
[ 56718-71-9 ]
(S)-5-((4-(2-methoxyethyl)phenoxy)methyl)-3-isopropyloxazolidin-2-one [ No CAS ]

Reference： [1]Organic Process Research and Development,2011,vol. 15,p. 1365 - 1370

78
[ 56718-71-9 ]
[ 1006885-95-5 ]

Reference： [1]Organic Process Research and Development,2011,vol. 15,p. 1365 - 1370

79
[ 56718-71-9 ]
(S)-metoprolol succinate [ No CAS ]

Reference： [1]Organic Process Research and Development,2011,vol. 15,p. 1365 - 1370

80
[ 56718-71-9 ]
[ 1393526-39-0 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 13554 - 13557

81
[ 56718-71-9 ]
[ 105780-38-9 ]

Reference： [1]Letters in Organic Chemistry,2012,vol. 9,p. 516 - 519

82
[ 56718-71-9 ]
[ 113798-78-0 ]

Reference： [1]Letters in Organic Chemistry,2012,vol. 9,p. 516 - 519

83
[ 56718-71-9 ]
[ 81024-42-2 ]

Reference： [1]Letters in Organic Chemistry,2012,vol. 9,p. 516 - 519
[2]Catalysis science and technology,2014,vol. 4,p. 3899 - 3908

84
[ 1430746-24-9 ]
[ 56718-71-9 ]
[ 1430745-54-2 ]

Yield	Reaction Conditions	Operation in experiment
30.7%	With di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; In tetrahydrofuran; at 20℃;Inert atmosphere;	To a solution of (lR,3s,5S)-tert-butyl 3-((ls,4S)-4-hydroxycyclohexyloxy)-8- azabicyclo[3.2.1]octane-8-carboxylate (300 mg, 0.922 mmol), <strong>[56718-71-9]4-(2-methoxyethyl)phenol</strong> (153 mg, 1.005 mmol), triphenylphosphine (270 mg, 1.029 mmol), and triethylamine (0.128 mL, 0.922 mmol) in 3 mL THF, diisopropyl diazene-l,2-dicarboxylate (0.218 mL, 1.107 mmol) was added slowly. After stirring at room temperature over night, solution was extracted with 1 M NaOH and CH2C12. Organic phases were concentrated and residue was purified by HPLC (H20/CH3CN gradient + 0.1% TFA). Fractions containing product were partly concentrated and residue was extracted with 1 M NaOH and CH2C12. Organic phases were dried over MgS04, filtered, and concentrated to give (lR,3s,5S)-tert-butyl 3-((lr,4R)-4-(4-(2-methoxyethyl)phenoxy)cyclohexyloxy)-8- azabicyclo[3.2.1]octane-8-carboxylate (130 mg, 0.283 mmol, 30.7%) as an thick oil. Exact mass calculated for C27H41N05: 459.3, found: LCMS m/z = 460.6 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 1.35-1.63 (m, 8H), 1.46 (s, 9H), 1.86-2.00 (m, 6H), 2.0-2.12 (m, 2H), 2.81 (t, = 7.1 Hz, 2H), 3.35 (s, 3H), 3.40-3.47 (m, 1H), 3.56 (t, = 7.1 Hz, 2H), 3.79-3.84 (m, 1H), 4.17-4.28 (m, 3H), 6.79-6.83 (m, 2H), 7.09-7.13 (m, 2H).

Reference： [1]Patent: WO2013/55910,2013,A1 .Location in patent: Page/Page column 117

85
[ 953422-33-8 ]
[ 616-38-6 ]
[ 56718-71-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With Amberlyst 15; for 36h;Reflux;	General procedure: Amberlyst 15 (0.05 mmol, 11 mg) was added to asolution of the alcohol (1.0 mmol) in DMC (5 mL). The reaction mixture wasstirred at reflux for 36 hours adding Amberlyst 15 every 12 hours. The organicsolvent was filtered and evaporated as an azeotropic mixture with MeOH(DMC:MeOH 1:3) to obtain the product as a gummy oil.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 5004 - 5006

86
[ 56718-71-9 ]
[ 244768-32-9 ]
[ 1448695-92-8 ]

Yield	Reaction Conditions	Operation in experiment
98.4%		General procedure: To a solution of hydroxybenzophenone or phenol derivatives (3) (1 mmol) in anhydrous DMF (3 mL), K2CO3 (2 mmol) was added at room temperature under N2. The mixture was stirred for 10 min and the corresponding 2a-c (1 mmol) was added, respectively. The reaction mixture was heated at 80 C for 5-15 h. Then, the mixture was poured into ice-cold H2O (30 mL) and the resulting precipitate was filtered off. The obtained solid was further washed with ice-cold water (10 mL). The crude products 1a-u were finally purified by silica column chromatography eluting with hexane/ethylacetate 5:1 to 1:1 to yield the pure compounds in 52.2%-98.4%.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 65,p. 134 - 143

87
4-(4-chloro-6-methyl-pyrimidin-2-ylamino)-benzonitrile [ No CAS ]
[ 56718-71-9 ]
[ 1448695-99-5 ]

Yield	Reaction Conditions	Operation in experiment
96.2%		General procedure: To a solution of hydroxybenzophenone or phenol derivatives (3) (1 mmol) in anhydrous DMF (3 mL), K2CO3 (2 mmol) was added at room temperature under N2. The mixture was stirred for 10 min and the corresponding 2a-c (1 mmol) was added, respectively. The reaction mixture was heated at 80 C for 5-15 h. Then, the mixture was poured into ice-cold H2O (30 mL) and the resulting precipitate was filtered off. The obtained solid was further washed with ice-cold water (10 mL). The crude products 1a-u were finally purified by silica column chromatography eluting with hexane/ethylacetate 5:1 to 1:1 to yield the pure compounds in 52.2%-98.4%.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 65,p. 134 - 143

88
[ 1140520-11-1 ]
[ 56718-71-9 ]
[ 1448696-06-7 ]

Yield	Reaction Conditions	Operation in experiment
94.0%		General procedure: To a solution of hydroxybenzophenone or phenol derivatives (3) (1 mmol) in anhydrous DMF (3 mL), K2CO3 (2 mmol) was added at room temperature under N2. The mixture was stirred for 10 min and the corresponding 2a-c (1 mmol) was added, respectively. The reaction mixture was heated at 80 C for 5-15 h. Then, the mixture was poured into ice-cold H2O (30 mL) and the resulting precipitate was filtered off. The obtained solid was further washed with ice-cold water (10 mL). The crude products 1a-u were finally purified by silica column chromatography eluting with hexane/ethylacetate 5:1 to 1:1 to yield the pure compounds in 52.2%-98.4%.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 65,p. 134 - 143

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P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
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

[ CAS No. 56718-71-9 ] {[proInfo.proName]}

Quality Control of [ 56718-71-9 ]

Related Doc. of [ 56718-71-9 ]

Product Details of [ 56718-71-9 ]

Calculated chemistry of [ 56718-71-9 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 56718-71-9 ]

Application In Synthesis of [ 56718-71-9 ]

[ 56718-71-9 ] Synthesis Path-Upstream 1~1

[ 56718-71-9 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 56718-71-9 ]

Aryls

Ethers

Precautionary Statements-General

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Physical hazards

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[ 56718-71-9 ]