15893-42-2|3-(4-Methoxyphenyl)propanoyl chloride| Ambeed

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Quality Control of [ 15893-42-2 ] Purity: 97% SDS Specification

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Product Details of [ 15893-42-2 ]

CAS No. :	15893-42-2
Formula :	C₁₀H₁₁ClO₂
M.W :	198.65
SMILES Code :	O=C(Cl)CCC1=CC=C(OC)C=C1
MDL No. :	MFCD02258671
InChI Key :	FQVJPHCAWYRYCK-UHFFFAOYSA-N
Pubchem ID :	10932441

Safety of [ 15893-42-2 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H314
Precautionary Statements:	P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501
Class:	8
UN#:	1760
Packing Group:	Ⅱ

Application In Synthesis of [ 15893-42-2 ]

* 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 [ 15893-42-2 ]

[ 15893-42-2 ] Synthesis Path-Downstream 1~38

1
[ 1929-29-9 ]
[ 15893-42-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With phosgene; In water monomer; at 20℃; for 4h;	General procedure: Cinnamoyl chlorides - Derivatives of cinnamic acid were stirred with oxalyl chloride (5 ml g-1) for up to 4 h. The stirring time differed depending on the dissolution rate of the starting cinnamic acid derivative. For derivatives with 4-NO2 or 4-N(CH3)2 substituents, a drop of dry N,N-DMF was added to catalyze the reaction. The excess reagent was evaporated under reduced pressure. The hydroxy groups in the hydroxycinnamic acid derivatives were acetylated prior to reaction with oxalyl chloride by stirring the derivative (0.0244 mol) in acetic anhydride (5 ml g-1) and pyridine (0.5 ml) at room temperature (rt, ~20 C) overnight. Cold water (~50 ml) was added to the mixture and stirred for further 5-10 min with cooling in an ice-water bath, and the resulting precipitate of acetoxycinnamic acid was obtained by vacuum filtration, washed with cold water and dried.Methyl N-cinnamoylanthranilates - The cinnamoyl chloride (0.014 mol) was added to a solution of excess methyl anthranilate (0.017 mol) in dry pyridine (10 ml g-1), and the mixture was stirred for an hour at rt. Cold water (250 ml) was added to the reaction mixture and the resulting precipitate was filtered and washed with cold water until free of pyridine, and was recrystallized from hot ethanol. In contrast, methyl N-hydrocinnamoylanthranilate derivatives, with a low melting point, were extracted in diethyl ether (2 × 70 ml), washed with cold water (2 × 50 ml) and the solvent evaporated under reduced pressure.N-Cinnamoylanthranilic acids - The methyl N-cinnamoylanthranilate (0.010 mol) was stirred in a mixture of THF (100 ml) and methanol (20 ml), and LiOH.H2O (0.050 mol) [LiOH dissolved in water 0.2 g per 10 ml] was added to the reaction mixture and stirred at rt overnight. The excess reagent and solvents were evaporated under reduced pressure. The crude product was dissolved in water (~350 ml) and acidified slowly to pH 4 using dilute HCl (1 M) with stirring. The precipitate was obtained by vacuumfiltration, washed with water and dried, and was recrystallized from hot aqueous ethanol (water-ethanol, 1:4). In the case of N-hydroxycinnamoylanthranilate derivatives, water was added to the resulting solution to aid crystallization.α-Methylcinnamic acid - To a mixture of benzaldehyde (5 ml, 0.0492 mol) and propionic anhydride61 (10 ml, 0.0780 mol), anhydrous sodium acetate (2.5 g) was added and heated under reflux for 4 h. Once the mixture has cooled down to rt, cold water (50 ml) was added and alkalized with saturated aqueous sodium carbonate (85 ml). The resulting solid suspension was heated up to dissolve completely, and the unreacted benzaldehyde was extracted in DCM (2 × 25 ml) and the aqueous layer was acidified with concentrated HCl (12 M) with cooling. The pale yellowish white crystals (yield 2.098 g, 26 %) of α-methylcinnamic acid was obtained by vacuum filtration, washed with little cold water (~10 ml) and dried.
	With thionyl chloride; In toluene;	a) Preparation of 3-(4-methoxyphenyl)propionyl Chloride To a suspension of 3-(4-methoxyphenyl)propionic acid (10 g) in 150 ml of toluene are added 8 ml of thionyl chloride and the mixture is heated to 65 C. for 4 hours. The solvent is evaporated off under reduced pressure and the residue is redissolved in toluene and concentrated to dryness. Such steo is repeated twice. 11 g of the product are obtained as a yellow oil.
	With thionyl chloride; In dichloromethane; for 3h;Reflux;	General procedure: A solution of 3-(4-fluorophenyl)propionic acid (300 mg, 1.8 mmol) in dry CH2Cl2 (20 mL) was treated with thionyl chloride (2.2 mL, 30.2 mmol). The reaction mixture was refluxed for 3 h and the solvent was then removed until dryness. A translucent oil, corresponding to 3-(4-fluorophenyl)propanoyl chloride, was obtained and used directly in the next reaction under the same conditions described in the general procedure.

	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 2h;	Step 1 Oxalyl chloride (5 eq) was added to a solution of 4-methoxyphenyl)propionic acid (1 eq) in CH2CI2 (0.1 M), and then a catalytic amount of DMF was added to the reaction mixture to initiate the reaction and bubbling occurred. The reaction was complete in 2 hours, and the solution was dried with N2 for one hour to give the acid chloride, which was used immediately in the next step.
	With thionyl chloride; In N,N-dimethyl-formamide; toluene; at 75℃; for 3h;	A solution of p-methoxyphenylpropionic acid (12a, 2.99 mmol), SOCl2 (2 mL) and DMF (2 drops) was added to toluene (20 mL) and stirred at 75C for 3 h. The reaction was terminated and the solution was concentrated to dryness under reduced pressure to give p-methoxyphenylpropionyl chloride (13a). (6,2.61 mmol), pyridine (1 mL) in CH2Cl2 (10 mL) was added dropwise with stirring Oxyphenylpropionyl chloride (13a). After completion of the dropwise addition, the reaction was refluxed for 2 h. The reaction was completed, cooled to room temperature, poured into dilute hydrochloric acid, stirred. Extracted with dichloromethane, and washed with saturated brine. The solvent was concentrated to dryness under reduced pressure to give crude product. Column chromatography (petroleum ether / ethyl acetate: 15/1, V / V) gave a white solid in 66.8%
	With phosphorus(V) chloride; In dichloromethane;Reflux;	General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%)
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 5h;	General procedure: An oven-dried flask was charged with aliphatic carboxylic acid (1.00 equiv) and CH2Cl2 (0.50 M). Three drops of N,N-dimethylformamide (DMF) and oxalyl chloride (1.20 equiv, 1.00 M) in DCM were added dropwise. The reaction mixture was stirred vigorously at room temperature for 5 h and then evaporated DCM and redundant oxalyl chloride under the vacuum. The crude acid chloride was used for the next reaction without any further purification
	With oxalyl dichloride; N,N-dimethyl-formamide; at 20℃; for 1h;Inert atmosphere;	General procedure: Oxalyl chloride (2equiv) was added at room temperature into asolutioncarboxylic acids(1equiv) in anhydrous dichloromethane. Added one drop ofN,N-dimethylformamide and reacted under nitrogen atmosphere for 1h. The solvent was removed under vacuum, yielding a crude product that were stored in a nitrogen atmosphere for subsequent use without further purified.

References: [1]European Journal of Medicinal Chemistry,2005,vol. 40,p. 764 - 771.
[2]Journal of the American Chemical Society,2015,vol. 137,p. 7656 - 7659.
[3]European Journal of Medicinal Chemistry,2019,vol. 170,p. 141 - 156.
[4]Organic Letters,2020,vol. 22,p. 2902 - 2907.
[5]Journal of the Chemical Society,1909,vol. 95,p. 1722.
[6]Journal of Medicinal Chemistry,1981,vol. 24,p. 451 - 454.
[7]Journal of Medicinal Chemistry,1986,vol. 29,p. 2465 - 2472.
[8]Phytochemistry,1981,vol. 20,p. 1097 - 1104.
[9]Journal of the Chemical Society. Perkin transactions I,1982,p. 2407 - 2412.
[10]Journal of Heterocyclic Chemistry,2003,vol. 40,p. 519 - 522.
[11]Synlett,2004,p. 477 - 480.
[12]Pharmazie,2004,vol. 59,p. 744 - 752.
[13]Journal of Medicinal Chemistry,2006,vol. 49,p. 1494 - 1498.
[14]Journal of Organic Chemistry,2000,vol. 65,p. 4179 - 4184.
[15]Journal of Organic Chemistry,2001,vol. 66,p. 7166 - 7177.
[16]Patent: US6110924,2000,A .
[17]Organic Letters,2008,vol. 10,p. 2601 - 2604.
[18]Patent: US6335332,2002,B1 .Location in patent: Page column 11.
[19]Organic and Biomolecular Chemistry,2009,vol. 7,p. 3561 - 3571.
[20]Journal of Medicinal Chemistry,2009,vol. 52,p. 3366 - 3376.
[21]Organic Letters,2010,vol. 12,p. 3990 - 3993.
[22]Molecular Crystals and Liquid Crystals,2011,vol. 545,p. 149 - 155.
[23]Journal of the American Chemical Society,2013,vol. 135,p. 7442 - 7445.
[24]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 3221 - 3230.
[25]Synlett,2012,vol. 23,p. 2389 - 2392.
[26]Organic Letters,2014,vol. 16,p. 1268 - 1268.
[27]Patent: WO2015/35051,2015,A1 .Location in patent: Page/Page column 232.
[28]Advanced Synthesis and Catalysis,2016,vol. 358,p. 887 - 893.
[29]Angewandte Chemie - International Edition,2016,vol. 55,p. 6988 - 6991.
    Angew. Chem.,2016,vol. 128,p. 7102 - 7105,4.
[30]Journal of the American Chemical Society,2017,vol. 139,p. 2200 - 2203.
[31]Patent: CN106146450,2016,A .Location in patent: Paragraph 0204; 0205; 0206.
[32]Angewandte Chemie - International Edition,2017,vol. 56,p. 12307 - 12311.
    Angew. Chem.,2017,vol. 129,p. 12475 - 12479,5.
[33]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 6267 - 6272.
[34]Journal of Medicinal Chemistry,2018,vol. 61,p. 5199 - 5221.
[35]Organic Letters,2019,vol. 21,p. 3625 - 3630.
[36]Tetrahedron,2019,vol. 75,p. 4186 - 4191.
[37]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 2327 - 2331.
[38]Journal of the American Chemical Society,2019,vol. 141,p. 16362 - 16373.
[39]Angewandte Chemie - International Edition,2021,vol. 60,p. 171 - 175.
    Angew. Chem.,2021,vol. 133,p. 173 - 177,5.
[40]Journal of Medicinal Chemistry,2021,vol. 64,p. 1844 - 1855.
[41]Organic Letters,2021,vol. 23,p. 3310 - 3314.
[42]Biomolecules,2022,vol. 12.
[43]Bioorganic and Medicinal Chemistry Letters,2022,vol. 64.

2
[ 15893-42-2 ]
[ 20401-88-1 ]

Yield	Reaction Conditions	Operation in experiment
44%	With iron(II) oxide; tris(2,4,6-trimethoxyphenyl)phosphine; phenylsilane; In toluene; at 60℃; for 2h;Inert atmosphere; Schlenk technique;	General procedure: A typical procedure for the iron oxide catalyzed reduction of 3-phenylpropionyl chloride (1a) with H3SiPh (Table1 , entry 1): iron oxide (3.6mg, 0.050mmol) and TMPP (6.7mg, 0.013mmol) were added to a 10mL Schlenk flask with a magnetic stir bar. The flask was evacuated and backfilled with argon three times. Then, H3SiPh (34μL, 0.28mmol) was added to the flask and the reaction mixture was stirred at 60C for 20h under an argon atmosphere. Then, toluene (0.50mL) was added to the flask and the resultant solution was stirred at room temperature for 5min before 1a (37μL, 0.25mmol) was loaded. Further, the reaction mixture was stirred at 60C for 20h under an argon atmosphere. After cooling to room temperature, the reaction mixture was diluted with diethyl ether (5.0mL) and tetradecane (50μL, 0.19mmol) as an internal standard was added. The yield of 3-phenylpropanal (2a; 57%) was analyzed by gas chromatography. 2a was isolated by silica gel column chromatography (hexane: EtOAc=13: 1). Pale yellow oil (16.8mg) was obtained in 50% yield.

References: [1]Synlett,2012,vol. 23,p. 2389 - 2392.
[2]Catalysis Communications,2014,vol. 50,p. 25 - 28.
[3]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1959,vol. 79,p. 1069,1072.
Chem.Abstr.,1960,p. 4561.
[4]Synlett,2006,p. 869 - 872.
[5]Synlett,2004,p. 477 - 480.

3
[ 15893-42-2 ]
[ 25413-27-8 ]

Yield	Reaction Conditions	Operation in experiment
33.4 mg	With ammonium hydroxide; In dichloromethane; at 0 - 20℃; for 0.333333h;	Step 2 Ammonium hydroxide (0.13 M) was added to a solution of acid chloride (1 eq) in CH2C12 (0.2 M) at 0 C. The reaction mixture stirred for 20 minutes at rt. The reaction mixture was extracted into CH2C12 and the organic layer was dried with Na2S04 and concentrated to give the amide as a white solid in 35% yield over 2 steps, 33.4 mg. 1H NMR (500 MHz, DMSO-d6) δ 7.27 (s, 1H), 7.12 - 7.08 (m, 2H), 6.84 - 6.79 (m, 2H), 6.78 - 6.73 (m, 1H), 3.70 (s, 3H), 2.71 (t, J= 7.7 Hz, 2H), 2.29 (t, J= 7.8 Hz, 2H). ESI-MS (m z): 180.0 [M+H]+.

References: [1]Journal of the Chemical Society,1930,p. 21,23.
[2]Journal of the Chemical Society,1909,vol. 95,p. 1722.
[3]Journal of Medicinal Chemistry,2009,vol. 52,p. 3366 - 3376.
[4]Patent: WO2015/35051,2015,A1 .Location in patent: Page/Page column 232.
[5]Angewandte Chemie - International Edition,2021,vol. 60,p. 171 - 175.
Angew. Chem.,2021,vol. 133,p. 173 - 177,5.

4
[ 15893-42-2 ]
[ 20387-29-5 ]

References: [1]Journal of the American Chemical Society,1968,vol. 90,p. 4038 - 4051.

5
[ 67-52-7 ]
[ 15893-42-2 ]
[ 113379-21-8 ]

References: [1]Journal of the American Chemical Society,1988,vol. 110,p. 2210.
[2]Patent: US6335332,2002,B1 .Location in patent: Page column 11.

6
[ 1143-38-0 ]
[ 15893-42-2 ]
[ 151562-49-1 ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 4099 - 4107.

7
[ 15893-42-2 ]
[ 96495-22-6 ]
[ 144181-33-9 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4408 - 4414.

8
[ 15893-42-2 ]
[ 593-56-6 ]
[ 103831-07-8 ]

References: [1]Journal of Organic Chemistry,1989,vol. 54,p. 3394 - 3403.
[2]Angewandte Chemie - International Edition,2021,vol. 60,p. 171 - 175.
Angew. Chem.,2021,vol. 133,p. 173 - 177,5.

9
[ 15893-42-2 ]
[ 142260-67-1 ]
[ 147862-36-0 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3156 - 3169.

10
[ 15893-42-2 ]
[ 13623-25-1 ]

References: [1]Journal of Organic Chemistry,1984,vol. 49,p. 2517 - 2520.
[2]Journal of Organic Chemistry,1970,vol. 35,p. 647 - 651.
[3]Molecular Crystals and Liquid Crystals,2011,vol. 545,p. 149 - 155.
[4]Journal of Medicinal Chemistry,2021,vol. 64,p. 1844 - 1855.

11
[ 15893-42-2 ]
[ 134-20-3 ]
[ 83988-43-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In water; at 20℃; for 1h;	General procedure: Cinnamoyl chlorides - Derivatives of cinnamic acid were stirred with oxalyl chloride (5 ml g-1) for up to 4 h. The stirring time differed depending on the dissolution rate of the starting cinnamic acid derivative. For derivatives with 4-NO2 or 4-N(CH3)2 substituents, a drop of dry N,N-DMF was added to catalyze the reaction. The excess reagent was evaporated under reduced pressure. The hydroxy groups in the hydroxycinnamic acid derivatives were acetylated prior to reaction with oxalyl chloride by stirring the derivative (0.0244 mol) in acetic anhydride (5 ml g-1) and pyridine (0.5 ml) at room temperature (rt, ~20 C) overnight. Cold water (~50 ml) was added to the mixture and stirred for further 5-10 min with cooling in an ice-water bath, and the resulting precipitate of acetoxycinnamic acid was obtained by vacuum filtration, washed with cold water and dried.Methyl N-cinnamoylanthranilates - The cinnamoyl chloride (0.014 mol) was added to a solution of excess methyl anthranilate (0.017 mol) in dry pyridine (10 ml g-1), and the mixture was stirred for an hour at rt. Cold water (250 ml) was added to the reaction mixture and the resulting precipitate was filtered and washed with cold water until free of pyridine, and was recrystallized from hot ethanol. In contrast, methyl N-hydrocinnamoylanthranilate derivatives, with a low melting point, were extracted in diethyl ether (2 × 70 ml), washed with cold water (2 × 50 ml) and the solvent evaporated under reduced pressure.N-Cinnamoylanthranilic acids - The methyl N-cinnamoylanthranilate (0.010 mol) was stirred in a mixture of THF (100 ml) and methanol (20 ml), and LiOH.H2O (0.050 mol) [LiOH dissolved in water 0.2 g per 10 ml] was added to the reaction mixture and stirred at rt overnight. The excess reagent and solvents were evaporated under reduced pressure. The crude product was dissolved in water (~350 ml) and acidified slowly to pH 4 using dilute HCl (1 M) with stirring. The precipitate was obtained by vacuumfiltration, washed with water and dried, and was recrystallized from hot aqueous ethanol (water-ethanol, 1:4). In the case of N-hydroxycinnamoylanthranilate derivatives, water was added to the resulting solution to aid crystallization.α-Methylcinnamic acid - To a mixture of benzaldehyde (5 ml, 0.0492 mol) and propionic anhydride61 (10 ml, 0.0780 mol), anhydrous sodium acetate (2.5 g) was added and heated under reflux for 4 h. Once the mixture has cooled down to rt, cold water (50 ml) was added and alkalized with saturated aqueous sodium carbonate (85 ml). The resulting solid suspension was heated up to dissolve completely, and the unreacted benzaldehyde was extracted in DCM (2 × 25 ml) and the aqueous layer was acidified with concentrated HCl (12 M) with cooling. The pale yellowish white crystals (yield 2.098 g, 26 %) of α-methylcinnamic acid was obtained by vacuum filtration, washed with little cold water (~10 ml) and dried.

References: [1]Journal of the Chemical Society. Perkin transactions I,1982,p. 2407 - 2412.
[2]European Journal of Medicinal Chemistry,2019,vol. 170,p. 141 - 156.

12
[ 15893-42-2 ]
[ 79315-43-8 ]
[ 289889-53-8 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3074 - 3084.

13
[ 15893-42-2 ]
(3R,4S)-1-Phenyl-4-trimethylsilanyl-hex-5-en-3-ol [ No CAS ]
[ 357914-68-2 ]

References: [1]Synlett,2001,p. 955 - 959.

14
[ 1117-96-0 ]
[ 15893-42-2 ]
[ 378233-70-6 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 7166 - 7177.

15
[ 15893-42-2 ]
[ 1117-97-1 ]
[ 749927-93-3 ]

References: [1]Organic Letters,2005,vol. 7,p. 1427 - 1429.

16
[ 31926-62-2 ]
[ 15893-42-2 ]
3-(4-methoxy-phenyl)-propionic acid naphtho[2,3-<i>b</i>]thiophen-4-yl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7816 - 7825.

17
[ 943-89-5 ]
[ 15893-42-2 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1494 - 1498.

18
[ 15893-42-2 ]
2-{2,5-dimethoxy-4-[3-(4-methoxy-phenyl)-propyl]-phenyl}-1-methyl-ethylamine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3074 - 3084.

19
[ 15893-42-2 ]
[ 1026133-26-5 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3074 - 3084.

20
[ 15893-42-2 ]
[ 113378-98-6 ]