[ CAS No. 104-20-1 ] {[proInfo.proName]}

Name: 104-20-1|4-(4-Methoxyphenyl)-2-butanone|97%
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Quality Control of [ 104-20-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 104-20-1 ]

Product Details of [ 104-20-1 ]

CAS No. :	104-20-1	MDL No. :	MFCD00008791
Formula :	C₁₁H₁₄O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PCBSXBYCASFXTM-UHFFFAOYSA-N
M.W :	178.23	Pubchem ID :	61007
Synonyms :	p-Methoxybenzylacetone

Calculated chemistry of [ 104-20-1 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.36
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	52.52
TPSA :	26.3 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) :	-5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.3
Log Po/w (XLOGP3) :	2.06
Log Po/w (WLOGP) :	2.22
Log Po/w (MLOGP) :	2.03
Log Po/w (SILICOS-IT) :	2.88
Consensus Log Po/w :	2.3

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.32
Solubility :	0.852 mg/ml ; 0.00478 mol/l
Class :	Soluble
Log S (Ali) :	-2.24
Solubility :	1.02 mg/ml ; 0.00574 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.67
Solubility :	0.0383 mg/ml ; 0.000215 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.19

Safety of [ 104-20-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 104-20-1 ]

* 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 [ 104-20-1 ]
Downstream synthetic route of [ 104-20-1 ]

[ 104-20-1 ] Synthesis Path-Upstream 1~3

1
[ 104-20-1 ]
[ 5471-51-2 ]

Reference： [1] Sci. Rep. Tohoku Univ., Ser. 1: Phys., Chem., Astron., vol. 7, p. 84

2
[ 153993-00-1 ]
[ 104-20-1 ]
[ 4133-34-0 ]

Reference： [1] Tetrahedron Letters, 1993, vol. 34, # 41, p. 6631 - 6634
[2] Journal of Organic Chemistry, 1998, vol. 63, # 9, p. 2867 - 2872

3
[ 104-20-1 ]
[ 4133-34-0 ]

Reference： [1] Journal of Organic Chemistry, 1998, vol. 63, # 9, p. 2867 - 2872
[2] Tetrahedron Letters, 1993, vol. 34, # 41, p. 6631 - 6634

[ 104-20-1 ] Synthesis Path-Downstream 1~43

1
[ 104-20-1 ]
[ 67952-38-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	With Poly(n-butyl-4-vinylpyridinium)borohydride; In ethanol; at 20℃; for 4.4h;	General procedure: To a solution of the substrate (1 mmol) in ethanol as asolvent (5 mL) in a round-bottomed flask (25 mL) equippedwith a magnetic stirrer, P(BVP)BH4 (100 mg) was addedand stirred at room temperature. The progress of thereaction was monitored by TLC. On completion of thereaction, the mixture was filtered and the used reagent waswashed successively with HCl (1.0 M, 2 10 mL) andethanol (2 5 mL). The combined filtrates were evaporatedand the pure product was obtained in moderate to excellent yields. In a few cases in which the reaction wasnot complete, the crude product was purified on silica gelwith an appropriate eluent (Scheme 1).
	With sodium tetrahydroborate;	General procedure: rac-3a and rac-4a were produced by reducing <strong>[104-20-1]4-(4'-methoxyphenyl)-2-butanone</strong> and 1-phenyl-2-butanone, respectively, with NaBH4 as reported [4]. NMR data for were consistent (rac)-3a and (rac)-4a were consistent those reported [3].

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 12593 - 12628
[2]Journal of the American Chemical Society,2014,vol. 136,p. 9521 - 9523
[3]Tetrahedron Letters,2001,vol. 42,p. 2137 - 2139
[4]Comptes Rendus Chimie,2014,vol. 17,p. 23 - 29
[5]Organic and Biomolecular Chemistry,2019,vol. 17,p. 1749 - 1753
[6]Comptes Rendus Chimie,2013,vol. 16,p. 721 - 727
[7]Annales de Chimie (Cachan, France),1925,vol. <10> 4,p. 423,435
[8]Tetrahedron Letters,1999,vol. 40,p. 1417 - 1418
[9]Journal of the Chemical Society. Perkin Transactions 1 (2001),2001,p. 2526 - 2531
[10]Journal of Organic Chemistry,2007,vol. 72,p. 30 - 34
[11]Journal of Organic Chemistry,2010,vol. 75,p. 2981 - 2988
[12]Journal of Molecular Catalysis B: Enzymatic,2015,vol. 115,p. 155 - 159
[13]Journal of the American Chemical Society,2016,vol. 138,p. 6139 - 6142
[14]Journal of the American Chemical Society,2016,vol. 138,p. 7520 - 7523
[15]RSC Advances,2016,vol. 6,p. 96616 - 96622
[16]Organic Letters,2017,vol. 19,p. 4413 - 4415
[17]European Journal of Organic Chemistry,2018,vol. 2018,p. 798 - 805

2
[ 104-20-1 ]
[ 5471-51-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With hydrogen bromide; acetic acid; In water; at 130℃; for 4h;	4-(4-Methoxyphenyl)-2-butanone (5.34 g, 30 mmol), glacial acetic acid (3 g, 50 mmol), 47% hydrobromic acid(10.47ml, 90mmol) was placed in a reaction flask, reacted at 130 C for 4 h, cooled, added water (30 mL), extracted with chloroform (30 mL)Take 3 times, combine the organic phase, concentrate, and acid-base treatment to obtain crude 4-p-hydroxyphenyl-2-butanone (4.5g), which is recrystallized to give 4-p-Hydroxyphenyl-2-butanone (Formula 1, 4.27 g, yield: 86%).

Reference： [1]Patent: CN109265330,2019,A .Location in patent: Paragraph 0022; 0055-0056; 0058-0061
[2]Sci. Rep. Tohoku Univ., Ser. 1: Phys., Chem., Astron.,vol. 7,p. 84

3
[ 36600-75-6 ]
[ 104-20-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium hydroxide; In water; at 80℃; for 3h;	A 10% aqueous sodium hydroxide solution (30 mL, 75 mmol) was added dropwise to the above solution containing ethyl 2-acetyl-3-(4-methoxyphenyl)propanoate.After stirring at 80 C for 3 h, cooled, concentrated hydrochloric acid (25 mL, 300 mmol).Dry over anhydrous sodium sulfate and concentrate to give crude 4-(4-methoxyphenyl)-2-butanone.Distillation under reduced pressure gave 4-(4-methoxyphenyl)-2-butanone (Formula 5, 4.4 g, yield: 82%).

Reference： [1]Patent: CN109265330,2019,A .Location in patent: Paragraph 0022; 0045; 0047; 0049; 0051; 0052; 0054
[2]Journal of the Chemical Society,1930,p. 2482,2486

4
[ 3815-30-3 ]
[ 104-20-1 ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 4738 - 4742
[2]Journal of Organic Chemistry,1998,vol. 63,p. 2867 - 2872
[3]Advanced Synthesis and Catalysis,2006,vol. 348,p. 354 - 360
[4]Organic and Biomolecular Chemistry,2006,vol. 4,p. 1650 - 1652
[5]Synlett,2005,p. 2449 - 2452
[6]Journal of labelled compounds and radiopharmaceuticals,2015,vol. 58,p. 479 - 482
[7]Sci. Rep. Tohoku Univ., Ser. 1: Phys., Chem., Astron.,vol. 7,p. 83
Chemisches Zentralblatt,1921,vol. 92,p. 1017
[8]Justus Liebigs Annalen der Chemie,1904,vol. 330,p. 233
[9]Journal of the Chemical Society. Perkin transactions I,1983,p. 2577 - 2582
[10]Journal of Organic Chemistry,2010,vol. 75,p. 2981 - 2988

5
[ 598-32-3 ]
[ 66107-29-7 ]
[ 104-20-1 ]
[ 141172-02-3 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3558 - 3563

6
[ 104-94-9 ]
[ 78-94-4 ]
[ 104-20-1 ]

Yield	Reaction Conditions	Operation in experiment
52%	With hydrogenchloride; iron; sodium nitrite; In water; acetone; at 0 - 20℃;	General procedure: To a suspended solution of aniline 1a-k (7.8 mmol) in HCl (10 ml, 6N), a solution of NaNO2 (1.4 g, 20.3 mmol) in water (5 ml) was added slowly over 30 minutes at 0 C. Meanwhile, in a two-necked round flask, fitted with condenser and gas bubbler, olefin (15.6 mmol) was dissolved in acetone (20 ml). The diazonium salt solution was added slowly to the stirred olefin solution through a septum by syringe. After complete addition, iron powder (0.88 g, 15.6 mmol) was added to the reaction mixture on 2-3 times. The reaction mixture was stirred at 0 C until the N2 evolving terminated, then the reaction mixture was removed from the ice and the stirring continued at rt for another 30 minutes to 1 h. After the reaction accomplished, the reaction mixture was quenched by water and ice and extracted by ethyl acetate. The products were obtained in pure form after purification by silica gel column chromatography using different eluent systems. The oximes were recrystallized from a proper solvent.

Reference： [1]Synthesis,1980,p. 291 - 292
[2]Synthetic Communications,2020,vol. 50,p. 526 - 538

7
[ 104-20-1 ]
[ 1477-68-5 ]
N-[1-methyl-3-(4-methoxyphenyl)propyl]-2-(3-methoxy-4-hydroxyphenyl)ethylamine hydrochloride [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,2001,vol. 51,p. 18 - 23

8
[ 104-20-1 ]
[ 645-33-0 ]
N-[1-methyl-3-(4-methoxyphenyl)propyl]-2-(3-hydroxy-4-methoxyphenyl)ethylamine hydrochloride [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,2001,vol. 51,p. 18 - 23

9
[ 943-88-4 ]
[ 104-20-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	With methanol; C25H29ClNO2Rh; potassium carbonate; at 90℃; for 1h;	A Radley tube was charged with an unsaturated ketone (0.3mmol), catalyst (0.003 mmol) and K2CO3 (0.25 eq), to which was introduced MeOH (1.5 mL). The reaction mixture was heated to reflux at 90 C for 1 h. The resulting mixture was then cooled to room temperature, followed by solvent evaporation under vacuum. The product was purified by flash column chromatography (hexane/ethyl acetate, 4:1).

Reference： [1]Advanced Synthesis and Catalysis,2007,vol. 349,p. 1949 - 1954
[2]European Journal of Organic Chemistry,2012,p. 2809 - 2815
[3]Journal of Nanoscience and Nanotechnology,2012,vol. 12,p. 2000 - 2007
[4]Organic Letters,2019,vol. 21,p. 5867 - 5872
[5]Organic Process Research and Development,2011,vol. 15,p. 858 - 870
[6]Russian Journal of Organic Chemistry,2001,vol. 37,p. 1534 - 1541
[7]Cuihua Xuebao/Chinese Journal of Catalysis,2019,vol. 40,p. 1795 - 1799
[8]Synthesis,2003,p. 2415 - 2426
[9]Advanced Synthesis and Catalysis,2013,vol. 355,p. 3648 - 3660
[10]Advanced Synthesis and Catalysis,2015,vol. 357,p. 4063 - 4068
[11]Medicinal Chemistry Research,2016,vol. 25,p. 1678 - 1685

10
[ 55831-55-5 ]
[ 104-20-1 ]

Yield	Reaction Conditions	Operation in experiment
88%	With Dimethylphenylsilane; C19H8O7Ru3; In 1,4-dioxane; at 50℃; for 1h;Inert atmosphere;	General procedure: In a 20 mL two-necked flask, (mu3, eta2, eta3, eta5 - acenaphthylene)Ru3(CO)7 (1 or 0.1 mol% to the vinyl ether) was dissolved in a minimum amount of dry dioxane. To this solution, hydrosilane (10~30 mol% to the vinyl ether) was added and the mixture was stirred at 50 C for 30 min. The initial orange color of the solution was darkened. Then, the vinyl ether was added dropwise and the mixture was stirred at 50 C. After the reaction, volatiles were removed under reduced pressure and the product was purified by chromatography (silica-gel) eluting with hexane/EtOAc to afford the product.

Reference： [1]Tetrahedron,2012,vol. 68,p. 3243 - 3252
[2]Advanced Synthesis and Catalysis,2002,vol. 344,p. 845 - 848
[3]Advanced Synthesis and Catalysis,2003,vol. 345,p. 1017 - 1030

11
[ 104-20-1 ]
[ 152339-86-1 ]
[ 39516-05-7 ]

Yield	Reaction Conditions	Operation in experiment
	With NADPH; nicotinamide adenine dinucleotide phosphate; W110G TeSADH; In acetonitrile; at 50℃;pH 8.0;Enzymatic reaction;	General procedure: Enantiopure alcohol (0.015 mmol), NADP+ (0.5 mg), NADPH (1.0 mg), mutant TeSADH (0.2 mg in Tris-HCl buffer solution, 50 mM, pH 8.0), Tris-HCl buffer solution (950 muL, 50 mM, pH 8.0), and acetonitrile (50 muL) were mixed in a 1.5-mL plastic tube. The reaction mixture was shaken at 50 C and 200 rpm for 48 h, followed by extraction with ethyl acetate (2 × 500 muL). The combined organic layer was dried with sodium sulfate and concentrated to dryness. The remaining residue was treated with pyridine (two drops) and acetic anhydride (one drop) for 1 h to convert the alcohols to their corresponding acetates. The acetate products were diluted with CHCl3 prior to analysis on a GC equipped with a chiral column to determine ee.

Reference： [1]Tetrahedron Asymmetry,2006,vol. 17,p. 268 - 274
[2]Journal of Organic Chemistry,2007,vol. 72,p. 30 - 34
[3]Angewandte Chemie - International Edition,2007,vol. 46,p. 3091 - 3094
[4]Advanced Synthesis and Catalysis,2012,vol. 354,p. 415 - 427
[5]ChemCatChem,2013,vol. 5,p. 3821 - 3828
[6]ChemCatChem,2013,vol. 5,p. 3821 - 3828
[7]Journal of Molecular Catalysis B: Enzymatic,2015,vol. 115,p. 155 - 159
[8]ChemCatChem,2016,vol. 8,p. 1459 - 1463
[9]Advanced Synthesis and Catalysis,2016,vol. 358,p. 4006 - 4018
[10]Advanced Synthesis and Catalysis,2016,vol. 358,p. 4006 - 4018
[11]European Journal of Organic Chemistry,2018,vol. 2018,p. 798 - 805

12
[ 104-20-1 ]
[ 14633-54-6 ]
4-(4-methoxy-phenyl)-2-(1-phenylsulfanyl-cyclopropyl)-butan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃;

Reference： [1]Alberti, Guido; Bernard, Angela M.; Frongia, Angelo; Piras, Pier Paolo; Secci, Francesco; Spiga, Marco [Synlett, 2006, # 14, p. 2241 - 2245]

13
[ 78-94-4 ]
[ 155826-85-0 ]
[ 104-20-1 ]

Yield	Reaction Conditions	Operation in experiment
41%	With water; diphenyl acetylene In 1,4-dioxane at 60℃; for 24h;

Reference： [1]Shirakawa, Eiji; Yasuhara, Yuichi; Hayashi, Tamio [Chemistry Letters, 2006, vol. 35, # 7, p. 768 - 769]

14
[ 104-20-1 ]
[ 152339-86-1 ]

Yield	Reaction Conditions	Operation in experiment
75.9%	With water; In ethanol; for 72h;modified Czepak Dox medium;	General procedure: The substrates (each 100 mg) in EtOH (1 mL) were added to the culture and shaken for the periods shown in the Tables. Substrate and organism controls were also run simultaneously in each case. At the end of fermentation, the mycelial mass was filtered from the culture medium. The filtrate was extracted with chloroform (2 × 50 mL), washed with H2O (2 × 20 mL) and dried. Removal of the solvent gave a residue which on preparative thin-layer chromatography (silica gel, EtOAc/hexane) furnished the respective product alcohols. The spectral and chiroptical data of compounds 1b, 2b, 4b, 7b and 9b matched those reported by us previously.9c
	With NADPH; nicotinamide adenine dinucleotide phosphate; W110A TeSADH; In isopropyl alcohol; at 50℃; for 10h;pH 8.0;Enzymatic reaction;	(S)-3a (91% ee) was prepared by W110A TeSADH-catalyzed reduction of <strong>[104-20-1]4-(4-methoxyphenyl)-2-butanone</strong> as follows: A mixture of <strong>[104-20-1]4-(4-methoxyphenyl)-2-butanone</strong> (50 mg, 0.28 mmol), NADP+ (2 mg), and W110A TeSADH (0.60 mg) in 10.0 mL of Tris-HCl buffer solution (50 mM, pH 8.0)/2-propanol (70:30, v/v) was placed in a round bottomed flask equipped with a condenser and a magnetic stirrer. The reaction mixture was stirred at 50C for 10 h then it was extracted with 3 × 5 mL ethyl acetate. The combined organic layers were dried with Na2SO4 and concentrated under vacuum. The remaining residue was purified with silica gel using hexane/ethyl acetate (85/15). A small fraction of the purified compound was treated with pyridine (2 drops) and acetic anhydride (1 drop) for 2 h to convert the produced alcohol to the corresponding acetate ester. The acetate ester was then analyzed by a GC equipped with a chiral column to confirm its ee. Spectral data for (S)-3a were consistent with that described above for (rac)-3a and that reported [3].

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 1512 - 1515
[2]Journal of Organic Chemistry,2007,vol. 72,p. 30 - 34
[3]Chemical Communications,2003,p. 2916 - 2917
[4]Organic and Biomolecular Chemistry,2008,vol. 6,p. 887 - 892
[5]Organic and Biomolecular Chemistry,2013,vol. 11,p. 2911 - 2915
[6]Journal of Molecular Catalysis B: Enzymatic,2015,vol. 115,p. 155 - 159

15
[ 104-20-1 ]
[ 1078-28-0 ]

Reference： [1]Synthesis,2003,p. 2415 - 2426
[2]Synthesis,2003,p. 2415 - 2426

16
[ 104-21-2 ]
[ 104-20-1 ]

Reference： [1]Advanced Synthesis and Catalysis,2003,vol. 345,p. 1017 - 1030

17
[ 104-20-1 ]
[ 120-20-7 ]
N-[1-methyl-3-(4-methoxyphenyl)propyl]-2-(3,4-dimethoxyphenyl)ethylamine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92.04%		Into a 500 ml three-necked flask, 216.0 ml of dichloromethane was sequentially added.After 18.0 g of anisylacetone (I), 18.0 g of acetic acid and 51.1 g of ammonium formate were uniformly stirred,Adding 18 g of 3,4-dimethoxyphenylethylamine (II) and 0.9 g of 5% palladium on carbon,The temperature was raised to reflux (40 C) and reacted for 3 hours. Cool down to 20 C - 30 C,The palladium carbon was filtered off, and the filtrate was adjusted to pH 7-8 with 150 ml of aqueous sodium hydroxide solution (2%). The dichloromethane layer was separated and the organic phase was washed once with 100 ml of water.The dichloromethane layer was collected. Add 18 ml of concentrated hydrochloric acid to the dichloromethane layer.After stirring for 1 hour, the layers were separated, and a dichloromethane layer was collected. Dichloromethane was distilled off.The crude yellow intermediate (III) was obtained. Add 180 ml of absolute ethanol to the crude product.Heat to reflux, stir and dissolve,The temperature was slowly lowered to 0 C to 5 C to precipitate a white solid. Filtered, vacuum dried,Intermediate (III) is obtained. The yield is 92.04%,The HPLC purity was 99.73%.
	With toluene-4-sulfonic acid;palladium; In water; toluene;	EXAMPLE 2 In a round bottom three necked flask equipped with a reflux condenser, a stirrer and a Dean-Starke water separator was placed 100 g. of <strong>[104-20-1]1-(4-methoxyphenyl)-3-butanone</strong>, 1 g. of p-toluenesulfonic acid, 110 g. of homoveratrylamine and 400 ml. of toluene. The solution which was obtained was heated at the reflux temperature for 3 hours. During this time the theoretical yield of water was collected in the water trap. The reaction mixture was then allowed to stir overnight. The reaction mixture was charged into a stainless steel hydrogenation bottle and 20 g. of 5 percent palladium on carbon catalyst were added. The reaction mixture was hydrogenated at a temperature of about 50 C. under a hydrogen pressure of 50 psi. The reduction was allowed to continue for 16 hours during which time the theoretical uptake of hydrogen was observed. The catalyst was filtered and anhydrous hydrogen chloride was passed through the filtrate until the saturation point was achieved. The acidified filtrate was then cooled and the reduction product began to precipitate as the hydrochloride salt. The addition of ether to the acidified filtrate facilitated the precipitation of the product. The crystalline precipitate was filtered to yield 148.3 g. of the reduction product, dl-3,4-dimethoxy-N-[3-(4-methoxyphenyl)-1-methyl-n-propyl]-beta-phenethylamine hydrochloride.

Reference： [1]Patent: CN109851511,2019,A .Location in patent: Paragraph 0015; 0017
[2]Patent: US3987200,1976,A

18
[ 943-88-4 ]
[ 104-20-1 ]
[ 100-66-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2007,vol. 349,p. 1949 - 1954

19
[ 104-20-1 ]
[ 72824-04-5 ]
[ 1071821-48-1 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 13824 - 13825

20
[ 104-20-1 ]
[ 857393-13-6 ]

Yield	Reaction Conditions	Operation in experiment
68%		4-(4-Methoxyphenyl)-2-aminobutane hydrochloride-Compound M (MGN-M253) (S. K. Chattopadhyay, K. V. Sashidhara, V. Koneni, V. Tripathi, A. K. Tripathi, V. Prajapati, S. Kumar, U. S. (2001) 6252114) A mixture of <strong>[104-20-1]4-(4-methoxyphenyl)-2-butanone</strong> (2.09 g, 11.74 mmol), ammonium acetate (9.06 g, 11.75 mmol) and sodium cyanoborohydride (0.52 g, 0.82 mmol) in methanol (30 ml) was stirred at room temperature for 72 h. The reaction mixture was acidified with concentrated HCl (10 ml) and the solvent remove in vacuo. Water was then added and the unreacted starting material was extracted using diethyl ether (3×50 ml). The aqueous solution was made basic using potassium hydroxide pellets, saturated with sodium chloride (2 g) and extracted with diethyl ether (3×100 ml). The combined organic extracts were dried with magnesium sulfate and evaporated in vacuo to give 3-(4-methoxyphenyl)-1-methylpropylamine as a colourless viscous liquid. The hydrochloride was then prepared by adding 20% HCl-methanol (3 ml) to the amine. The mixture was evaporated to dryness and recrystallised from dichloromethane to give 3-(4-methoxyphenyl)-1-methylpropylamine hydrochloride as a white solid (0.31 g, 68%).numax(film)/cm-1 1514, 1612, 2937, 2997, 3423 (N-H stretch).1H NMR (300 MHz; CDCl3) 1.52 (3H, d, J 6.6 Hz), 2.09 (2H, m), 2.88 (2H, m), 3.66 (1H, m), 4.01 (3H, s), 7.17 (2H, d, J 8.7 Hz), 7.45 (2H, d, J 8.7 Hz);13C NMR (75 MHz; CDCl3) 17.7, 30.1, 36.0, 47.6, 55.7, 114.5, 129.8, 133.9, 157.5;m/z (ES+) 180 ([M-Cl]+, 100%);m/z HRMS calcd for C11H18NO [M+H]+ 180.13883. found 180.13863.

Reference： [1]Patent: US2009/221702,2009,A1 .Location in patent: Page/Page column 7

21
[ 104-20-1 ]
[ 107-21-1 ]
[ 290309-44-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	With 9,10-dihydro-10-methylacridine; at 80℃; for 24h;Green chemistry;	To a four-necked flask equipped with a stirrer and a thermometer was added 4- (4-methoxyphenyl) -2-butanone (0.2 mol, 33 g), hydrogen-supported catalyst AcrH20.52 g of ethylene glycol and 100 mL of ethylene glycol were stirred at 80 C for 24 h. After the completion of the reaction, the excess ethylene glycol alcohol was extracted by distilled water and the extract was distilled under reduced pressure to obtain 38.1 g of a pale yellow liquid in 86% yield.
68%	With eosin y; at 90℃;Inert atmosphere; Schlenk technique; Irradiation;	General procedure: A 25-mL oven-dried Schlenk tube was sequentially added a mixture of aldehyde derivatives (0.5 mmol), dry CH3OH (2 mL), and Eosin Y (6.4 mg, 2 mol%). The tube was evacuated and backfilled with nitrogen (three times). The reaction mixture was stirred under a 16 W LED white lamp irradiation at a distance of 10 cm at room temperature for 12 h. The resulting mixture was diluted with EtOAc (8 mL). After completion of the reaction, phenylhydrazine was added to react with the excess benzaldehyde. The resulting crude product was washed with sodium hydroxide solution thrice. Subsequently, anhydrous sodium sulfate was added to remove water and the resulting mixture was filtered to collect the filtrate. The solvent in the filtrate was partially removed by rotary evaporation and the remaining product was purified by column chromatography (ethyl acetate/petroleum ether), followed by another round of rotary evaporation to afford the corresponding compounds.
	With camphor-10-sulfonic acid; In toluene;Inert atmosphere; Reflux;	General procedure: A 500 mL flask equipped with a Dean-Stark apparatus was charged with ketone (0.1 mol), ethylene glycol (31 g, 0.5 mol) or catechol (16.5 g, 0.15 mol), camphor-10-sulfonic acid (1 g, 4.3 mmol), and toluene (200 mL). The mixture was refluxing, and completion of the reaction was followed by TLC. Then, for the preparation of ethylene ketals, the solution was washed with saturated aqueous solution of NaHCO3, and dried over MgSO4. For the preparation of dioxoles, the solution was stirred for 2 h with anhydrous K2CO3 (15 g) and then filtered. The solvent was evaporated in vacuo, and the residue was flash chromatographed on silica gel.

Reference： [1]Patent: CN105859496,2016,A .Location in patent: Paragraph 0092-0097
[2]Synthetic Communications,2018,vol. 48,p. 1068 - 1075
[3]Tetrahedron,2011,vol. 67,p. 1448 - 1455

22
[ 591-50-4 ]
[ 86549-27-1 ]
[ 104-20-1 ]
(E)-ethyl 3,3-dimethyl-5-phenylpent-4-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: iodobenzene; 2,2-dimethylpent-4-enoic acid ethyl ester With palladium diacetate In N,N-dimethyl-formamide Stage #2: 4-(4-methoxyphenyl)-2-butanone In tetrahydrofuran; mineral oil for 18h;

Reference： [1]Location in patent: experimental part Vadola, Paul A.; Carrera, Ignacio; Sames, Dalibor [Journal of Organic Chemistry, 2012, vol. 77, # 16, p. 6689 - 6702]

23
[ 24680-50-0 ]
[ 104-20-1 ]
(E)-2,3-bis(4-methoxyphenyl)-6-(4-methoxystyryl)-4-oxocyclohexanecarbaldehyde [ No CAS ]