35553-92-5|Ethyl 2-(3-methoxyphenyl)acetate| Ambeed

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Quality Control of [ 35553-92-5 ] Purity: 98% SDS Specification

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Product Details of [ 35553-92-5 ]

CAS No. :	35553-92-5
Formula :	C₁₁H₁₄O₃
M.W :	194.23
SMILES Code :	O=C(OCC)CC1=CC=CC(OC)=C1
MDL No. :	MFCD00026897
InChI Key :	XXVVNHCWPHMLEZ-UHFFFAOYSA-N
Pubchem ID :	2774971

Safety of [ 35553-92-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P264-P270-P301+P312-P330

Application In Synthesis of [ 35553-92-5 ]

* 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 [ 35553-92-5 ]

[ 35553-92-5 ] Synthesis Path-Downstream 1~35

1
[ 64-17-5 ]
[ 35553-92-5 ]
[ 5020-41-7 ]

References: [1]Journal of the Chemical Society,1935,p. 1533,1543.

2
[ 64-17-5 ]
[ 1798-09-0 ]
[ 35553-92-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	sulfuric acid;Heating / reflux;	(3-methoxy)phenylacetic acid (4.164 g, 25.06 mmol) was refluxed in EtOH in presence of catalytic amount of conc. H2SO4. The mixture was concentrated in vacuo, diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine. It was dried over Na2SO4 and concentrated to give colorless oil (4.69 g, 97%).
93%	With sulfuric acid; for 6h;Reflux;	General procedure: Step 1: A mixture of appropriate carboxylic acid (1 equiv) in ethanol was refluxed for6 h in the presence of a catalytic amount of H2SO4. After the reaction was finished,the cooled mixture was concentrated in vacuo. The mixture was diluted with ethylacetate and washed with NaHCO3 1% aqueous solution (10 mlx3), and brine (10mlx3). The combined organic layers were dried over Na2SO4, and evaporated togive crude product. The pure crude product was used without further purification.
93%	With sulfuric acid; for 6h;Reflux;	General procedure: Step 1: A mixture of appropriate carboxylic acid (1 equiv) in ethanol was refluxed for6 h in the presence of a catalytic amount of H2SO4. After the reaction was finished,the cooled mixture was concentrated in vacuo. The mixture was diluted with ethylacetate and washed with NaHCO3 1% aqueous solution (10 mlx3), and brine (10mlx3). The combined organic layers were dried over Na2SO4, and evaporated togive crude product. The pure crude product was used without further purification.

81%	With sulfuric acid; at 0 - 70℃; for 2h;	To a stirred solution of 3-methoxy-2-phenylacetic acid (5 g, 30 mmol) in absolute ethanol (50 ml), sulfuric acid (0.3 ml) was added at 0 C and reaction mixture was refluxed at 70 C for 2 hours. Reaction progress was monitored by TLC. After completion of the reaction, ethanol was removed by evaporation under reduced pressure. Then reaction mixture was neutralized with saturated solution of sodium bicarbonate and extracted with DCM (2 x 15 ml), dried over anhydrous Na2S04 and concentrated under reduced pressure to afford the title compound (3.82 g, 81 %) as colorless liquid. LCMS: m/z = 195.26 [M+l].
81%	With sulfuric acid; at 70℃; for 2h;	[00149] To a stirred solution of 3-methoxy-2-phenylacetic acid (5 g, 30 mmol) in absolute ethanol (50 ml), sulfuric acid (0.3 ml) was added at 0 C and reaction mixture was refluxed at 70 C for 2 hours. Reaction progress was monitored by TLC. After completion of the reaction, ethanol was removed by evaporation under reduced pressure. Then reaction mixture was neutralized with saturated solution of sodium bicarbonate and extracted with DCM (2 x 15 ml), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the title compound (3.82 g, 81 %) as colorless liquid. LCMS: m/z = 195.26 [M+1].
	With hydrogenchloride; In water monomer;Reflux;	To a solution of 3-methoxyphenylacetic acid (1 g, 6.02 mmol) in ethanol (10 mL) was added cHCl (5 drops) and the mixture heated at reflux overnight. The solvents were evaporated to give the target compound as a white solid. This compound was then dissolved in ethanol (10 mL) and hydrazine hydrate (5.86 mL, 120 mmol) was added and the mixture heated at reflux overnight. Solvents were evaporated and the product was purified by flash chromatography using a gradient mixture of ethyl acetate and hexanes to give the desire compound as a white solid (1.03 g, 94% over 2 steps). 1H NMR (CDCl3), δ 3.79 (s, 3H), 3.83 (s, 2H), 6.83 (m, 4H); MS m/z = 181.5 (M + H)+.
	With hydrogenchloride; In water monomer; for 18h;Reflux;	General procedure: To a stirred solution of carboxylic acid 11j-r (1 mmol) in EtOH(3 mL) was added conc. HCl (1 drop), and the resulting mixturewas refluxed for 18 h. After cooling, the solvent was removed, andthen the residue was added sat. NaHCO3 aq., and the aqueous mixturewas extracted with CH2Cl2. The organic extracts were driedover Na2SO4, and the solvent was removed to afford the correspondingethyl ester, which was used for the next reaction withoutfurther purification. To a stirred solution of ethyl ester (1 mmol),obtained above, in EtOH (0.5 mL) was added hydrazine monohydrate(0.05 mL, 1 mmol), and the resulting mixture was refluxedfor 18 h. The solvent was removed to give the corresponding acylhydrazide, which was used for the next reaction without furtherpurification. To a stirred solution of acylhydrazide, obtained above,in CH2Cl2 (1 mL) was added a solution of isothiocyanate 8a-h or10c, i (1 mmol) in CH2Cl2 (5 mL), and the resulting mixture was stirredat room temperature for 18 h. The insoluble solid was correctedby filtration, and dried to give acyl hydrazino thiourea 13A-U.

References: [1]Patent: US2007/244094,2007,A1 .Location in patent: Page/Page column 53-54.
[2]Journal of Organic Chemistry,2001,vol. 66,p. 7818 - 7824.
[3]Bioorganic Chemistry,2022,vol. 123.
[4]Bioorganic Chemistry,2022,vol. 123.
[5]Patent: WO2019/161162,2019,A1 .Location in patent: Paragraph 00104; 00164-00165.
[6]Patent: WO2021/21893,2021,A1 .Location in patent: Paragraph 00147-00149.
[7]Journal of the Chemical Society. Perkin transactions I,1985,p. 2677 - 2688.
[8]Journal of the American Chemical Society,1949,vol. 71,p. 1922,1924.
[9]Bulletin de la Societe Chimique de France,1972,p. 306 - 317.
[10]Journal of Fluorine Chemistry,1990,vol. 49,p. 115 - 126.
[11]Journal of Medicinal Chemistry,1988,vol. 31,p. 2015 - 2021.
[12]Marine Drugs,2014,vol. 12,p. 1839 - 1858.
[13]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 3736 - 3745.
[14]Journal of the American Chemical Society,2021.

3
[ 35553-92-5 ]
[ 141-43-5 ]
(3-methoxy-phenyl)-acetic acid-(2-hydroxy-ethylamide) [ No CAS ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 2837,2842.

4
[ 50-00-0 ]
[ 35553-92-5 ]
[ 200214-17-1 ]

Yield	Reaction Conditions	Operation in experiment
33%	With sodium hydrogencarbonate; In dimethyl sulfoxide; at 17 - 60℃; for 27h;	Intermediate 31 Ethyl 3-hydroxy-2-(3-methoxyphenyl)propanoateEthyl 2-(3-methoxyphenyl)acetate (1.0 g, 5.149 mmol) was weighed into a round bottom flask with sodium hydrogen carbonate (0.02 g, 0.257 mmol). DMSO (8 mL) was added followed by paraformaldehyde (0.39 mL, 5.149 mmol). The resultant suspension was allowed to stir at room temperature for 24 hours then the reaction was heated at 60 C. for 3 hours to give a colourless solution. The reaction mixture was cooled, diluted with water (100 mL) and neutralised with 0.5 M HCl. The aqueous was extracted with EtOAc (3*50 mL), dried (MgSO4) and evaporated under reduced pressure to give a colourless oil which was purified by FCC (SiO2, 0-50% EtOAc in cyclohexane). The solvent was removed under reduced pressure to provide ethyl 3-hydroxy-2-(3-methoxyphenyl)propanoate as a colourless oil (0.38 g, 33%). 1H NMR (400 MHz, CDCl3, 21 C.) δ1.23 (3H, t), 2.26 (1H, s), 3.86-3.76 (5H, m), 4.28-4.06 (3H, m), 6.89-6.79 (3H, m), 7.30-7.22 (1H, m). m/z: ES+ [M+H]+ 225.

References: [1]Chemical and Pharmaceutical Bulletin,1982,vol. 30,p. 428 - 439.
[2]Patent: US2017/152255,2017,A1 .Location in patent: Paragraph 0327; 0328.

5
[ 35553-92-5 ]
[ 130754-15-3 ]

References: [1]Journal of Fluorine Chemistry,1990,vol. 49,p. 115 - 126.

6
[ 35553-92-5 ]
[ 75-07-0 ]
[ 115981-89-0 ]

References: [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 2015 - 2021.

7
[ 35553-92-5 ]
[ 105-58-8 ]
[ 50874-07-2 ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 745 - 747.
[2]Heterocycles,1996,vol. 43,p. 1031 - 1047.
[3]Journal of the American Chemical Society,2021.

8
[ 35553-92-5 ]
[ 74-88-4 ]
[ 105166-35-6 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1985,p. 2677 - 2688.

9
[ 35553-92-5 ]
[ 107-12-0 ]
[ 87942-68-5 ]

References: [1]Journal of Chemical Research, Miniprint,1983,p. 1601 - 1624.

10
[ 35553-92-5 ]
[ 75-36-5 ]
[ 63476-11-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrogenchloride;AlCl3; In CS2;	Ethyl 2'-acetyl-5'-methoxyphenylacetate (50) Acetyl chloride (21.3 mL, 300 mmol) was added to a mixture of AlCl3 (26.7 g, 200 mmol) and ethyl 3'-methoxyphenylacetate (49, 28.66 g, 147.6 mmol) in CS2 (200 mL) at 0 C. The ice bath was removed and the mixture was allowed to warm to 20 C. with HCl gas bubbling out. After stirring at 20 C. for 30 min, the mixture was refluxed for 30 min. Upon cooling down, the mixture was added ice (200 g) and aqueous 2 N HCl (400 mL). The resulting mixture was extracted with ethyl acetate (2200 mL). The extracts were washed with water (2100 mL), dried over MgSO4 and concentrated in vacuo. The residue was crystallized from a mixture of ethyl acetate (20 mL) and hexanes (60 mL) to afford 50 (30.60 g, 88%): 1H NMR (CDCl3) δ7.84 (1H, d, J=8.6 Hz), 6.86 (1H, dd, J=8.6, 2.6 Hz), 6.75 (1H, d, J=2.6 Hz), 4.17 (2H, q, J=7.1 Hz), 3.92 (2H, s), 3.86 (3H, s), 2.55 (3H, s), 1.28 (3H, t, J=7.1 Hz); 13C NMR (CDCl3) δ199.04 (s), 171.44 (s), 162.22 (s), 137.70 (s), 132.97 (d), 129.48 (s), 118.68 (d), 111.84 (d), 60.60 (t), 55.39 (q), 41.17 (t), 28.39 (q), 14.24 (q).

References: [1]Patent: US6482943,2002,B1 .
[2]European Journal of Medicinal Chemistry,1977,vol. 12,p. 161 - 171.
[3]Journal of Organic Chemistry,2001,vol. 66,p. 7818 - 7824.

11
[ 35553-92-5 ]
[ 200354-53-6 ]
3-(2-methoxycarbonylamino-phenyl)-2-(3-methoxy-phenyl)-3-oxo-propionic acid ethyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 4567 - 4569.

12
[ 35553-92-5 ]
[ 243841-37-4 ]
3-(4-chloro-2-ethoxycarbonylamino-phenyl)-2-(3-methoxy-phenyl)-3-oxo-propionic acid ethyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 4567 - 4569.

13
[ 35553-92-5 ]
[ 109-94-4 ]
[ 92848-09-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium; In diethyl ether; at 0 - 20℃;	General procedure: To a solution of ester 8 (20 mmol) in anhydrous ethyl ether was added ethyl formate (3.2 mL,40 mmol) at 0oC. Then sodium (0.92 g, 40 mmol) was added slowly. The reaction mixture wasstirred at room temperature. After completion of the reaction, the mixture was poured into icewater and extracted with Et2O (3×30 mL). The aqueous phase was acidified with a solution of 2NHCl to PH 3. Followed an extraction with Et2O (3×30 mL) and the organic layers were combined,dried over Na2SO4, filtered and concentrated in vacuum, leading to aldehyde 9 as a yellow oil which was used in the next step without further purification. Then 9 was dissolved in anhydrousdichloromethane and p-methoxyaniline (2.95 g, 24 mmol) was added, the reaction mixture wasstirred overnight at room temperature, the solvent was evaporated and the residue was subjected tochromatography to afford -enamino ester 1.

References: [1]ChemMedChem,2010,vol. 5,p. 1373 - 1385.
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4735 - 4739.
[3]Synlett,2014,vol. 25,p. 1879 - 1882.

14
[ 35553-92-5 ]
[ 877814-98-7 ]

Yield	Reaction Conditions	Operation in experiment
32%	With chlorosulfonic acid; In dichloromethane; at 0 - 30℃; for 1.16667h;	At 0 C., a solution of chlorosulfonic acid (5.5 mL, 79 mmol) in dichloromethane (10 mL) was added dropwise into a solution of ethyl 2-(3-methoxyphenyl)acetate 32a (5.02 g, 25.8 mmol) in dichloromethane (20 mL), the mixture was stirred for 10 min, and then moved to rt and stirred for 1 hour. The reaction mixture was poured into ice-water (10 mL), the organic layer was washed with water (10 mL), saturated sodium carbonate solution (10 mL) and saturated sodium chloride (10 mL) in turn, dried over anhydrous sodium sulfate. The mixture was filtered by suction filtration. The filtrate was concentrated to give the title compound 32b (2.39 g, yield: 32%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm) 7.66 (d, J=8.3 Hz, 1H), 6.80-6.71 (m, 2H), 4.07-3.96 (m, 4H), 3.74 (s, 3H), 1.17 (t, J=7.1 Hz, 3H).

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 854 - 858.
[2]Patent: US2020/377461,2020,A1 .Location in patent: Paragraph 0282; 0287; 0553-0555.

15
[ 765302-52-1 ]
4-acetyl-3-methoxy-phenylacetate [ No CAS ]
[ 35553-92-5 ]
2-[3-(3-chloro-5-cyano-phenoxy)-4-ethyl-phenyl]-N-(4-sulfamoyl-phenyl)-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13.96 g (69.5%)	With acetyl chloride;tin(IV) chloride; In dichloromethane;	Alternatively, 12a can be prepared by the procedures in steps 1-3 of example 6 except diethylzinc was used in place of dimethylzinc in step 2 To a stirred solution of ethyl 3-methoxyphenylacetate (16.0 g; 82.38 mmol) in CH2Cl2 (200 mL) at rt was added dropwise AcCl (9.88 mL; 138.9 mmol) followed by stannic chloride (16.9 mL; 169 mmol; 1.0 M solution in CH2Cl2). The reaction mixture was stirred at rt for 6 h and poured into an ice-water mixture. The aqueous phase was extracted with CH2Cl2 and the combined extracts were washed with water, dried (Na2SO4) and the solvent removed in vacuo. The crude product 8 was purified by chromatography on silica gel and eluding with CH2Cl2:EtOAc (20:1) to yield 13.96 g (69.5%) of a white solid.

References: [1]Patent: US2005/239880,2005,A1 .

16
[ 529-28-2 ]
ethyl lithioacetate [ No CAS ]
[ 35553-92-5 ]

References: [1]Organic Letters,1999,vol. 1,p. 1973 - 1975.

17
[ 35553-92-5 ]
3,4-dimethyl-7-methoxy-2-naphthol [ No CAS ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 7818 - 7824.

18
[ 35553-92-5 ]
[ 118964-06-0 ]