4038-15-7|(2,4-Dimethoxyphenyl)(4-methoxyphenyl)methanone| Ambeed

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Quality Control of [ 4038-15-7 ] Purity: 95% SDS Specification

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Product Details of [ 4038-15-7 ]

CAS No. :	4038-15-7
Formula :	C₁₆H₁₆O₄
M.W :	272.30
SMILES Code :	O=C(C1=CC=C(OC)C=C1)C2=CC=C(OC)C=C2OC
MDL No. :	MFCD00100089
InChI Key :	VFTDVICZBGDMMB-UHFFFAOYSA-N
Pubchem ID :	254174

Safety of [ 4038-15-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 4038-15-7 ]

* 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 [ 4038-15-7 ]

[ 4038-15-7 ] Synthesis Path-Downstream 1~35

1
[ 4038-15-7 ]
phenylmagnesium bromide [ No CAS ]
[ 102751-95-1 ]

References: [1]Journal of the Chemical Society,1957,p. 3757,3760.

2
[ 4038-15-7 ]
[ 1470-79-7 ]

References: [1]Journal of the American Chemical Society,1949,vol. 71,p. 3663.

3
[ 4038-15-7 ]
[ 53039-53-5 ]

References: [1]Journal of the Chemical Society,1957,p. 3755.

4
[ 100-07-2 ]
[ 151-10-0 ]
[ 4038-15-7 ]

Yield	Reaction Conditions	Operation in experiment
	aluminium trichloride; In hexane; dichloromethane;	Step 1 1,3 dimethoxybenzene (57.0 grams, 0.41 mole) and p-anisoyl chloride (69.0 grams, 0.41 mole) were added to a reaction flask containing 1000 milliliters of methylene chloride. Aluminum chloride (61.0 grams, 0.45 mole) was added slowly and the resulting mixture was stirred for 4 hours under a nitrogen atmosphere. The reaction mixture was added to a 10 weight percent aqueous hydrochloric acid solution containing ice and stirred for about thirty minutes. The organic layer was separated and the aqueous layer was back extracted with 100 milliliters of methylene chloride. The organic portions were combined and washed with water and washed again with a dilute sodium hydroxide solution. The organic layer was dried over magnesium sulfate and the residual methylene chloride was removed under vacuum. The resulting oily product (96.0 grams) solidified upon standing. The solid was crushed, added to hexane, filtered, washed with hexane, and dried. The resulting product, 2,4,4'-trimethoxy-benzophenone was not purified further but used directly in the next step.
	aluminium trichloride; In dichloromethane;	Step 1 1,3-Dimethoxybenzene (13.8 grams, 0.1 mole) and p-anisoyl chloride (17 grams, 0.1 mole) were dissolved in 200 milliliters of methylene chloride and stirred at room temperature. Anhydrous aluminum chloride (15 grams) was added slowly to the reaction mixture over a period of 15 minutes with stirring. After stirring an additional 15 minutes, the contents of the flask were carefully poured into 200 milliliters of a mixture of ice and dilute hydrochloric acid. The organic fraction was separated and washed with water. The solvent was removed on a rotary evaporator leaving an oily product that solidified on standing. This solid was broken-up, washed with two 50 milliliter portions of pentane, and dried, yielding 2,4,4'-trimethoxybenzophenone.
		1, 3-Dimethoxybenzene (13.8 g) and p-anisoyl chloride (17 g) were dissolved in a reaction flask containing 200 mL of methylene chloride and stirred at room temperature. Anhydrous aluminum chloride (15 g) was added slowly to the reaction mixture over a period of 15 minutes with stirring. After stirring an additional 15 minutes, the contents of the flask were carefully poured into 200 mL of a mixture of ice and dilute hydrochloric acid. The organic fraction was separated and washed with water. The solvent was removed on a rotary evaporator leaving an oily product that solidified on standing. This solid was broken-up, washed with two 50 rnL portions of pentane, and dried, yielding (2,4-dimethoxy- phenyl) - (4-methoxy-phenyl)-methanone.

References: [1]Chemische Berichte,1922,vol. 55,p. 2273.
[2]Patent: US5411679,1995,A .
[3]Patent: US5466398,1995,A .
[4]Patent: WO2005/61514,2005,A1 .Location in patent: Page/Page column 44-45.

5
[ 39828-35-8 ]
[ 100-66-3 ]
[ 4038-15-7 ]

References: [1]Chemische Berichte,1910,vol. 43,p. 1889.

6
[ 4038-15-7 ]
(aminooxy)acetic acid hemihydrochloride [ No CAS ]
[1-(2,4-Dimethoxy-phenyl)-1-(4-methoxy-phenyl)-meth-(Z)-ylideneaminooxy]-acetic acid [ No CAS ]
[1-(2,4-Dimethoxy-phenyl)-1-(4-methoxy-phenyl)-meth-(E)-ylideneaminooxy]-acetic acid [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1980,vol. 57,p. 1244 - 1247.

7
[ 4038-15-7 ]
[ 23997-81-1 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1980,vol. 19,p. 1074 - 1075.

8
[ 4038-15-7 ]
[ 6131-38-0 ]

References: [1]Tetrahedron,1996,vol. 52,p. 13623 - 13640.

9
[ 100-09-4 ]
[ 151-10-0 ]
[ 4038-15-7 ]

Yield	Reaction Conditions	Operation in experiment
73%	With poly phosphoric acid; at 80℃; for 1.5h;	General procedure: In order to prepare PPA (polyphosphoric acid), a mixture of H3PO4 (6.4 g) and P2O5 (11.5 g) in 150 mL beaker was stirred at 80 C for 15 min. 1-Bromo-3-methoxybenzene (9) (3.08 g,16.47 mmol) and 3,4-dimethoxybenzoic acid (7) (2 g, 10.98 mmol) were added to prepared PPA solution and the mixture was stirred with a glass stick at 80 C for 1.5 h. After the completion of the reaction, cold water was added to the reaction mixture and then the organic layer was extracted with EtOAc (3 150 mL). The combined organic phases were dried over Na2SO4 and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography with silica gel (30 g) by eluting with hexane:ethyl acetate (9:1). Recrystallization of the solid with hexane-ethyl acetate gave 2-bromo-4-methoxyphenyl)(3,4-dimethoxyphenyl)methanone (10) (2.32 g) as a white solid with 60% yield.

References: [1]Tetrahedron,1996,vol. 52,p. 13623 - 13640.
[2]Bioorganic Chemistry,2015,vol. 60,p. 49 - 57.
[3]Journal of Organic Chemistry,2020,vol. 85,p. 10772 - 10796.
[4]Archiv der Pharmazie,2018,vol. 351.

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone; for 8h;Reflux;	General procedure: 2.00 g of 2,2',4,4'-tetrahydroxybenzophenone, 3.68 g of dimethyl sulfate and 4.03 g of potassium carbonate are dissolved in 12.0 g of acetone. The mixture is stirred at reflux temperature for 8 hours. Then, the mixture is cooled to 25 C., 60.0 g of water is added, and the precipitate is filtered by further stirring for 10 minutes. The precipitate is then dissolved in 20.0 g of ethyl acetate and the organic phase is washed with water. Thereafter, the ethyl acetate was distilled off, and the obtained product was purified by recrystallization using 15.0 g of ethanol. Thereby 1.40 g of 2,2 ', 4,4'-tetramethoxybenzophenone is obtained

11
[ 4038-15-7 ]
β.β-diphenyl-vinyl magnesium bromide [ No CAS ]
1-(2,4-dimethoxy-phenyl)-1-(4-methoxy-phenyl)-3,3-diphenyl-allyl alcohol [ No CAS ]

References: [1]Justus Liebigs Annalen der Chemie,1923,vol. 434,p. 60.

12
[ 4038-15-7 ]
[ 77901-45-2 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1980,vol. 19,p. 1074 - 1075.

13
[ 4038-15-7 ]
1-(2,4-dimethoxy-phenyl)-1-(4-methoxy-phenyl)-3,3-diphenyl-allene [ No CAS ]

References: [1]Justus Liebigs Annalen der Chemie,1923,vol. 434,p. 60.

14
[ 4038-15-7 ]
[ 1066-26-8 ]
[ 159595-96-7 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; xylene; at 20℃; for 24h;	A reaction flask was charged with 10 g of (2,4- dimethoxy-phenyl)- (4-methoxy-phenyl)-methanone as prepared in Step 1 of Part B of Example 10,150 mL of tetrahydrofuran, and 14.0 g of 18 weight percent slurry of sodium acetylide in xylene/mineral oil. The reaction mixture was stirred at room temperature under a nitrogen atmosphere for 24 hours. The contents of the flask were poured into a 500 mL beaker containing ice water and extracted three times with 100 mL portions of methylene chloride. The extracts were combined, dried over anhydrous magnesium sulfate and the solvent was removed under vacuum. The product was shown by NMR to have a structure consistent with 1- (2, 4-dimethoxy-phenyl)-l- (4- methoxy)-2-propyn-1-ol.

References: [1]Patent: WO2005/61514,2005,A1 .Location in patent: Page/Page column 47-48.

15
[ 91-52-1 ]
[ 4038-15-7 ]

Yield	Reaction Conditions	Operation in experiment
43%	With PPA; In methoxybenzene;	Step 6a: 2,4,4'-trimethoxybenzophenone. To a reaction flask were added 5.0 g (0.030 mole) of 2,4-dimethoxybenzoic acid, 3.25 g (0.030 mole) of anisole and 30 g of polyphosphoric acid. The reaction mixture was warmed to 60-70C with stirring for 2 hours and transferred into ice water. The resulting oil was extracted with ethyl acetate, the organic layer was separated, dried, evaporated and the resulting crude product was purified by column chromatography on silica using a 4:1 mixture of toluene and ethyl acetate as eluent. A light-yellow powder (3.5 g, 43%) was produced.

References: [1]Patent: EP1038870,2000,A1 .

16
[ 4038-15-7 ]
[ 159595-96-7 ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide;	Step 6b: 1-(2,4-dimethoxyphenyl)-1-(4-methoxyphenyl)-2-propyn-1-ol. To a solution of 2 g (0.022 mole) of lithium acetylide ethylenediamine complex in 10 ml dry dimethyl sulphoxide was added dropwise a solution of 6 g (0.022 mole) of <strong>[4038-15-7]2,4,4'-trimethoxybenzophenone</strong> in 20 ml of dry dimethyl sulphoxide over 1.5 hours at 60C. The resultant solution was stirred 1 hour at 60C and was then transferred into cold water. The resulting oil was extracted with ethyl acetate, the organic layer was separated, dried, evaporated. The crude product (a light-yellow oil, 5 g, 77 %) was used without additional purification.

References: [1]Patent: EP1038870,2000,A1 .

17
[ 26939-18-4 ]
[ 4038-15-7 ]
C₂₄H₃₁NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		2,4, 4,6-Tetramethyl-5, 6-dihydro-1, 3-oxazine (14. 1 g) was added to a reaction flask containing anhydrous THF (lOOmL). The stirred solution was cooled to-78C and n-' butyllithium (0.11 mole) -in hexane was added. After 2 hours, 27 g of the (2,4-dimethoxy-phenyl)- (4-methoxy-phenyl) - methanone produced in Step 1 of this Part B in 30 mL of anhydrous THF was added into the mixture over a period of 30 minutes. The reaction mixture was allowed to slowly ambient temperature for 2 hours. The mixture was then poured into 100 mL of ice water and acidified with concentrated HCl. The acidic solution was extracted with hexane and made basic by the addition of 40% NaOH solution. The resulting oil was extracted with ether, dried, and evaporated to produce a dihydrooxazine which was not purified but used directly in the next step.

References: [1]Patent: WO2005/61514,2005,A1 .Location in patent: Page/Page column 45.

18
[ 20469-63-0 ]
[ 5720-07-0 ]
[ 82102-37-2 ]
[ 4038-15-7 ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 10310 - 10318.

19
[ 4038-15-7 ]
(5-bromo-2,4-dimethoxyphenyl)(4-methoxyphenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With bromine; In chloroform; at 25℃; for 12h;	General procedure: To a solution of (2,4-dimethoxyphenyl)(4-methoxyphenyl)-methanone (18) (0.5 g, 1.84 mmol) in CHCl3 (50 mL) was added asolution of Br2 (0.29 g, 1.85 mmol) in CHCl3 (40 mL) at rt. The reaction mixture was stirred at rt for 12 h. After completion of the reaction,the solvent was evaporated under reduced pressure. The crystallization of the residue with ethyl acetate-hexane furnished(5-bromo-2,4-dimethoxyphenyl)(4-methoxyphenyl)methanone(19) (0.4 g, 62% yield) as a white solid. Mp: 135-137 C. 1H NMR(400 MHz, CDCl3): d 7.76 (d, 2H, A part of AB system, J = 8.9 Hz),7.53 (s, 1H), 6.90 (d, 2H, B part of AB system, J = 8.9 Hz), 6.52 (s,1H), 3.96 (s, 3H), 3.86 (s, 3H), 3.74 (s, 3H). 13C NMR (100 MHz,CDCl3): d 193.0, 163.7, 158.7, 158.6, 134.3, 132.4, 131.1, 123.0,113.7, 102.3, 96.9, 56.6, 56.3, 55.7. IR (cm1, CH2Cl2): 3003, 2966,2933, 2837, 1632, 1587, 1507, 1458, 1433, 1387, 1310, 1282,1253, 1210, 1169, 1018, 969, 902. Anal. Calcld. for C16H15BrO4: C54.72; H 4.31; Found: C 54.67; H 4.38.

References: [1]Bioorganic Chemistry,2015,vol. 60,p. 49 - 57.

20
[ 4038-15-7 ]
(5-bromo-2,4-dihydroxyphenyl)(4-hydroxyphenyl)methanone [ No CAS ]

References: [1]Bioorganic Chemistry,2015,vol. 60,p. 49 - 57.

21
[ 4038-15-7 ]
(2,4-dimethoxyphenyl)-(4'-methoxyphenyl)-methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.90 g	With sodium tetrahydroborate; potassium hydroxide; In methanol; for 3h;Reflux;	Synthesis of (2,4-dimethoxyphenyl)-(4’-methox- yphenyl)-methanolExample 110055] 1.0 g of 2,4-dimethoxy-4’-methoxybenzophenone and 0.01 g of potassium hydroxide are dissolved in 12.0 g of methanol. 0.42 g of sodium boron hydride is added to the methanol solution. The mixture is stirred at reflux temperature for 3 hours. Since then, the mixture is added to the 80 g of water, then extracted with 20.0 g ethyl acetate and the organic phase is washed with watet Thereafter, ethyl acetate is distilled away. Thereby, 0.90 g of (2,4-dimethoxyphenyl)- (4’-methoxyphenyl)-methanol is obtained.

References: [1]Patent: US2016/194300,2016,A1 .Location in patent: Paragraph 0055.

22
1-(4-methoxybenzoyl)piperidine-2,6-dione [ No CAS ]
[ 109384-40-9 ]
[ 4038-15-7 ]

References: [1]Chemistry - A European Journal,2016,vol. 22,p. 10420 - 10424.

23
[ 100-07-2 ]
[ 4038-15-7 ]

References: [1]Chemistry - A European Journal,2016,vol. 22,p. 10420 - 10424.

24
[ 17715-69-4 ]
[ 4038-15-7 ]

References: [1]Chemistry - A European Journal,2016,vol. 22,p. 10420 - 10424.

25
[ 1470-79-7 ]
[ 77-78-1 ]
[ 4038-15-7 ]

Yield	Reaction Conditions	Operation in experiment
1.43 g	With potassium carbonate; In acetone; for 8h;Reflux;	Synthesis of2,4-dimethoxy-4’-methoxybenzophenone10054] 2.00 g of 2,4-dihydroxy-4’-hydroxybenzophenone,1.95 g of dimethyl sulfate and 2.14 g of potassium carbonate are dissolved in 16.0 g of acetone. The mixture is stirred at reflux temperature for 8 hours. Since then, the mixture is cooled to 25 degrees Celsius and thrther stirred after addition of 80.0 g of water, then extracted with 20.0 g ethyl acetate and the organic phase is washed with watet Thereafter, ethyl acetate is distilled away, and the resultant is purified by silica gel colunm chromatography (ethyl acetate:hexane=3:97). Thereby, 1.43 g of 2, 4-dimethoxy-4’-methoxybenzophenone is obtained.

References: [1]Patent: US2016/194300,2016,A1 .Location in patent: Paragraph 0054.

26
[ 4038-15-7 ]
(E)-(2,4-dimethoxyphenyl)(4-methoxyphenyl)methanone oxime [ No CAS ]
(Z)-(2,4-dimethoxyphenyl)(4-methoxyphenyl)methanone oxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; hydroxylamine hydrochloride; In methanol; for 4h;Reflux;	General procedure: The oximes used as starting materials in this work were readily prepared by heating at reflux the corresponding aldehydes or ketones with 2.5 eq. of hydroxylamine hydrochloride in the presence of 2.2 eq. of pyridine, in methanol for 4 hours, based on a modified version of previously reported methods.

References: [1]Tetrahedron Letters,2019,vol. 60,p. 1636 - 1639.

27
[ 4038-15-7 ]
8-bromo-3-(2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-3H-naphtho[2,1-b]pyran [ No CAS ]