939-57-1|(E)-3-(o-Tolyl)acrylic acid| Ambeed

Structure of 939-57-1

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Quality Control of [ 939-57-1 ] Purity: 97% SDS Specification

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Product Details of [ 939-57-1 ]

CAS No. :	939-57-1
Formula :	C₁₀H₁₀O₂
M.W :	162.19
SMILES Code :	O=C(O)/C=C/C1=CC=CC=C1C
MDL No. :	MFCD00016841
InChI Key :	RSWBWHPZXKLUEX-VOTSOKGWSA-N
Pubchem ID :	819020

Safety of [ 939-57-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H332
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501

Application In Synthesis of [ 939-57-1 ]

* 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.

Downstream synthetic route of [ 939-57-1 ]

[ 939-57-1 ] Synthesis Path-Downstream 1~36

1
[ 64-17-5 ]
[ 939-57-1 ]
[ 24393-48-4 ]

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 1120 - 1123.
[2]Organic and Biomolecular Chemistry,2016,vol. 14,p. 2498 - 2503.
[3]Chemische Berichte,1938,vol. 71,p. 1563,1570.
[4]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2442 - 2446.

2
[ 939-57-1 ]
[ 22084-89-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen; potassium hydroxide; In water; at 20℃; under 760.051 Torr; for 1h;Green chemistry;	General procedure: 1.0 mmol, 0.148 g), catalyst BPPd(0)Si (5 mol%, 0.0836 g), andKOH (1.0 equiv., 5 mL 0.2 M solution) were added to the reactionflask under hydrogen gas (1 atm). The reaction mixture was stirredat room temperature for 30 min followed by catalyst filtration andwashing with 10 mL of water and ethyl acetate. The pH was adjusted to 2e3 using 1 N HCl. The organic phase was collectedafter solvent extraction from ethyl acetate and dried over MgSO4and in vacuo. The product was purified by silica-gel column chromatographyand analyzed by 1H NMR spectroscopy.
98%	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃;	Briefly, into a 250-mL round-bottom flask, was placed a solution of 2- methylbenzaldehyde (8 g, 66.58 mmol, 1.00 equiv) in ethanol (80 mL), malonic acid (7.6 g, 73.03 mmol, 1.10 equiv), Pyridine (5 mL). The resulting solution was heated to reflux for 48 hr and allowed to cool to room temperature. The crystalline mass which formed was collect by filtration and washed with ethanol. This resulted in 6 g (55%) of (E -3-o- tolylacrylic acid as a white solid. Next, into a 250-mL round-bottom flask was placed a solution of (is)-3-o-tolylacrylic acid (12 g, 73.99 mmol, 1.00 equiv) in methanol (80 mL), Palladium carbon (2 g, 10%). Hydrogen was bubbled into the solution and the resulting solution was stirred overnight at room temperature. The solids were filtered out and the residue was concentrated under vacuum. This resulted in 12 g (98%) of 3-o-tolylpropanoic acid as colorless oil. Next, a solution of 3-o-tolylpropanoic acid (12 g, 73.08 mmol, 1.00 equiv) in TfOH (70 mL) was placed into a 250-mL round-bottom flask. The resulting solution was stirred overnight at room temperature. Then, ice-water was added and extracted with DCM. The combined organic phases were dried over anhydrous Na2S04. After filtration and concentration, the residue was applied onto a silica gel column with EA/PE=1/100 to 1/50. This resulted in 10.6 g (98%) of 4-methyl-2,3-dihydroinden-l-one as a white solid. Next, a solution of l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazole (270 mg, 1.36 mmol, 1.00 equiv) in tetrahydrofuran (15 mL) was placed into a 100-mL 3- necked round-bottom flask. This was followed by the addition of n-BuLi (0.55 mL, 2.5M) with dropwise under N2 and stirred for 1 h at -70C. To this was added 4-methyl-2,3- dihydroinden-l-one (200 mg, 1.37 mmol, 1.00 equiv) in tetrahydrofuran (5 mL) dropwise. The reaction mixture was warmed to room temperature over a period of 1 h and the mixture was continued to stir overnight at rt. Then water was added and extracted with EA. The combined organic phases were dried over anhydrous a2S04. After filtration and concentration, the residue was purified by MPLC. This resulted in 250 mg (53%) of 4- methyl- 1 -(1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-imidazol-2-yl)-2,3 -dihydro- 1 H-inden- l-ol as colorless oil. Finally, a solution of 4-methyl-l-(l-((2- (trimethylsilyl)ethoxy)methyl)- 1 H-imidazol-2-yl)-2,3 -dihydro- 1 H-inden- 1 -ol ( 100 mg, 0.29 mmol, 1.00 equiv) in HCOOH (10 mL), Palladium carbon (10 mg) was placed into a 100 mL round bottom flask. The resulting solution was heated to reflux for one overnight. The pH value of the solution was adjusted to 8 with aqueous sodium bicarbonate solution and extracted with EA. The combined organic phases were dried over anhydrous Na2S04. After filtration and concentration, the residue was purified by MPLC. This resulted in 40 mg (67%) of 2-(4-methyl-2,3-dihydro-lH-inden-l-yl)-lH-imidazole as a white solid. LCMS(m/e) 199 (M+H); XH NMR (300 MHz, CDC13) delta ppm 6.96-7.18 (m, 3H), 6.93 (s, 2H), 4.59 (t, J=8.1 Hz, 1H), 2.80-3.00 (m, 2H), 2.50-2.62 (m, 1H), 2.29 (s, 3H), 2.45-2.29 (s, 1H).
98%	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃;	Briefly, into a 250-mL round-bottom flask, was placed a solution of 2-methylbenzaldehyde (8 g, 66.58 mmol, 1.00 equiv) in ethanol (80 mL), malonic acid (7.6 g, 73.03 mmol, 1.10 equiv), Pyridine (5 mL). The resulting solution was heated to reflux for 48 hr and allowed to cool to room temperature. The crystalline mass which formed was collect by filtration and washed with ethanol. This resulted in 6 g (55%) of (E)-3-o-tolylacrylic acid as a white solid. Next, into a 250-mL round-bottom flask was placed a solution of (E)-3-o-tolylacrylic acid (12 g, 73.99 mmol, 1.00 equiv) in methanol (80 mL), Palladium carbon (2 g, 10%). Hydrogen was bubbled into the solution and the resulting solution was stirred overnight at room temperature. The solids were filtered out and the residue was concentrated under vacuum. This resulted in 12 g (98%) of 3-o-tolylpropanoic acid as colorless oil. Next, a solution of 3-o-tolylpropanoic acid (12 g, 73.08 mmol, 1.00 equiv) in TfOH (70 mL) was placed into a 250-mL round-bottom flask. The resulting solution was stirred overnight at room temperature. Then, ice-water was added and extracted with DCM. The combined organic phases were dried over anhydrous Na2SO4. After filtration and concentration, the residue was applied onto a silica gel column with EA/PE=1/100 to 1/50. This resulted in 10.6 g (98%) of 4-methyl-2,3-dihydroinden-1-one as a white solid. Next, a solution of 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (270 mg, 1.36 mmol, 1.00 equiv) in tetrahydrofuran (15 mL) was placed into a 100-mL 3-necked round-bottom flask. This was followed by the addition of n-BuLi (0.55 mL, 2.5M) with dropwise under N2 and stirred for 1 h at -70 C. To this was added 4-methyl-2,3-dihydroinden-1-one (200 mg, 1.37 mmol, 1.00 equiv) in tetrahydrofuran (5 mL) dropwise. The reaction mixture was warmed to room temperature over a period of 1 h and the mixture was continued to stir overnight at rt. Then water was added and extracted with EA. The combined organic phases were dried over anhydrous Na2SO4. After filtration and concentration, the residue was purified by MPLC. This resulted in 250 mg (53%) of 4-methyl-1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)-2,3-dihydro-1H-inden-1-ol as colorless oil. Finally, a solution of 4-methyl-1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)-2,3-dihydro-1H-inden-1-ol (100 mg, 0.29 mmol, 1.00 equiv) in HCOOH (10 mL), Palladium carbon (10 mg) was placed into a 100 mL round bottom flask. The resulting solution was heated to reflux for one overnight. The pH value of the solution was adjusted to 8 with aqueous sodium bicarbonate solution and extracted with EA. The combined organic phases were dried over anhydrous Na2SO4. After filtration and concentration, the residue was purified by MPLC. This resulted in 40 mg (67%) of 2-(4-methyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole as a white solid. LCMS (m/e) 199 (M+H); 1H NMR (300 MHz, CDC3) delta ppm 6.96-7.18 (m, 3H), 6.93 (s, 2H), 4.59 (t, J=8.1 Hz, 1H), 2.80-3.00 (m, 2H), 2.50-2.62 (m, 1H), 2.29 (s, 3H), 2.45-2.29 (s, 1H).

Pd-C; In tetrahydrofuran;

Methyl-benzenepropanoic acid See W. E. Backmann and E. K. Raunio, J. Amer. Chem. Soc., 72:2530 (1950). A mixture of 14.5 g (8.95 mmol) of trans-2-methylcinnamic acid in 200 ml of THF and 1.0 g 5% Pd-C was hydrogenated at room temperature (three atmospheres). The mixture was filtered and the pale yellow filtrate was evaporated to give 14.5 g of a tan solid suitable for use in the next step. An analytical sample was obtained by recrystallization from n-hexane; mp 101-103.

References: [1]Journal of Organometallic Chemistry,2017,vol. 846,p. 296 - 304.
[2]Patent: WO2013/74892,2013,A1 .Location in patent: Page/Page column 39-40.
[3]Patent: US9125407,2015,B2 .Location in patent: Page/Page column 27; 28; 30.
[4]Tetrahedron Letters,2008,vol. 49,p. 6137 - 6140.
[5]Australian Journal of Chemistry,1959,vol. 12,p. 453,457.
[6]Journal of the American Chemical Society,1957,vol. 79,p. 240,242.
[7]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1519 - 1522.
[8]Patent: US5177075,1993,A .

3
[ 939-57-1 ]
[ 87212-80-4 ]

References: [1]Journal of the Chemical Society,1955,p. 461,464.
Journal of the Chemical Society,1959,p. 1027,1030.
[2]Synthetic Communications,1999,vol. 29,p. 4179 - 4185.

4
[ 141-82-2 ]
[ 529-20-4 ]
[ 939-57-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With pyridine;Reflux;	To a stirred solution of o-methylbenzaldehyde (50 g, 417 mmol) in pyridine (2 equiv, 65 mL) was added malonic acid (86.6 g, 834 mmol) and the mixture was refluxed for 4-5 h. The reaction mixture was then poured into ice-water followed by 1N HCl. The white solid precipitated out was filtered, washed with water and concentrated under high vacuum for 3-4 h to get the desired product (57 g, 87%).
87%	With pyridine;Reflux;	lntermediate-1 : o-Methylcinnamic acid: To a stirred solution of o-methylbenzaldehyde (50 g, 417 mmol) in pyridine (2 equiv, 65 ml_) was added malonic acid (86.6 g, 834 mmol) and the mixture was refluxed for 4-5 h. The reaction mixture was then poured into ice-water followed by 1 N HCI. The white solid precipitated out was filtered, washed with water and concentrated under high vacuum for 3-4 h to get the desired product (57 g, 87%).
55%	With pyridine; In ethanol; for 48h;Reflux;	Briefly, into a 250-mL round-bottom flask, was placed a solution of 2- methylbenzaldehyde (8 g, 66.58 mmol, 1.00 equiv) in ethanol (80 mL), malonic acid (7.6 g, 73.03 mmol, 1.10 equiv), Pyridine (5 mL). The resulting solution was heated to reflux for 48 hr and allowed to cool to room temperature. The crystalline mass which formed was collect by filtration and washed with ethanol. This resulted in 6 g (55%) of (E -3-o- tolylacrylic acid as a white solid. Next, into a 250-mL round-bottom flask was placed a solution of (is)-3-o-tolylacrylic acid (12 g, 73.99 mmol, 1.00 equiv) in methanol (80 mL), Palladium carbon (2 g, 10%). Hydrogen was bubbled into the solution and the resulting solution was stirred overnight at room temperature. The solids were filtered out and the residue was concentrated under vacuum. This resulted in 12 g (98%) of 3-o-tolylpropanoic acid as colorless oil. Next, a solution of 3-o-tolylpropanoic acid (12 g, 73.08 mmol, 1.00 equiv) in TfOH (70 mL) was placed into a 250-mL round-bottom flask. The resulting solution was stirred overnight at room temperature. Then, ice-water was added and extracted with DCM. The combined organic phases were dried over anhydrous Na2S04. After filtration and concentration, the residue was applied onto a silica gel column with EA/PE=1/100 to 1/50. This resulted in 10.6 g (98%) of 4-methyl-2,3-dihydroinden-l-one as a white solid. Next, a solution of l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazole (270 mg, 1.36 mmol, 1.00 equiv) in tetrahydrofuran (15 mL) was placed into a 100-mL 3- necked round-bottom flask. This was followed by the addition of n-BuLi (0.55 mL, 2.5M) with dropwise under N2 and stirred for 1 h at -70C. To this was added 4-methyl-2,3- dihydroinden-l-one (200 mg, 1.37 mmol, 1.00 equiv) in tetrahydrofuran (5 mL) dropwise. The reaction mixture was warmed to room temperature over a period of 1 h and the mixture was continued to stir overnight at rt. Then water was added and extracted with EA. The combined organic phases were dried over anhydrous a2S04. After filtration and concentration, the residue was purified by MPLC. This resulted in 250 mg (53%) of 4- methyl- 1 -(1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-imidazol-2-yl)-2,3 -dihydro- 1 H-inden- l-ol as colorless oil. Finally, a solution of 4-methyl-l-(l-((2- (trimethylsilyl)ethoxy)methyl)- 1 H-imidazol-2-yl)-2,3 -dihydro- 1 H-inden- 1 -ol ( 100 mg, 0.29 mmol, 1.00 equiv) in HCOOH (10 mL), Palladium carbon (10 mg) was placed into a 100 mL round bottom flask. The resulting solution was heated to reflux for one overnight. The pH value of the solution was adjusted to 8 with aqueous sodium bicarbonate solution and extracted with EA. The combined organic phases were dried over anhydrous Na2S04. After filtration and concentration, the residue was purified by MPLC. This resulted in 40 mg (67%) of 2-(4-methyl-2,3-dihydro-lH-inden-l-yl)-lH-imidazole as a white solid. LCMS(m/e) 199 (M+H); XH NMR (300 MHz, CDC13) delta ppm 6.96-7.18 (m, 3H), 6.93 (s, 2H), 4.59 (t, J=8.1 Hz, 1H), 2.80-3.00 (m, 2H), 2.50-2.62 (m, 1H), 2.29 (s, 3H), 2.45-2.29 (s, 1H).

55%	With pyridine; In ethanol; for 48h;Reflux;	Briefly, into a 250-mL round-bottom flask, was placed a solution of 2-methylbenzaldehyde (8 g, 66.58 mmol, 1.00 equiv) in ethanol (80 mL), malonic acid (7.6 g, 73.03 mmol, 1.10 equiv), Pyridine (5 mL). The resulting solution was heated to reflux for 48 hr and allowed to cool to room temperature. The crystalline mass which formed was collect by filtration and washed with ethanol. This resulted in 6 g (55%) of (E)-3-o-tolylacrylic acid as a white solid. Next, into a 250-mL round-bottom flask was placed a solution of (E)-3-o-tolylacrylic acid (12 g, 73.99 mmol, 1.00 equiv) in methanol (80 mL), Palladium carbon (2 g, 10%). Hydrogen was bubbled into the solution and the resulting solution was stirred overnight at room temperature. The solids were filtered out and the residue was concentrated under vacuum. This resulted in 12 g (98%) of 3-o-tolylpropanoic acid as colorless oil. Next, a solution of 3-o-tolylpropanoic acid (12 g, 73.08 mmol, 1.00 equiv) in TfOH (70 mL) was placed into a 250-mL round-bottom flask. The resulting solution was stirred overnight at room temperature. Then, ice-water was added and extracted with DCM. The combined organic phases were dried over anhydrous Na2SO4. After filtration and concentration, the residue was applied onto a silica gel column with EA/PE=1/100 to 1/50. This resulted in 10.6 g (98%) of 4-methyl-2,3-dihydroinden-1-one as a white solid. Next, a solution of 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (270 mg, 1.36 mmol, 1.00 equiv) in tetrahydrofuran (15 mL) was placed into a 100-mL 3-necked round-bottom flask. This was followed by the addition of n-BuLi (0.55 mL, 2.5M) with dropwise under N2 and stirred for 1 h at -70 C. To this was added 4-methyl-2,3-dihydroinden-1-one (200 mg, 1.37 mmol, 1.00 equiv) in tetrahydrofuran (5 mL) dropwise. The reaction mixture was warmed to room temperature over a period of 1 h and the mixture was continued to stir overnight at rt. Then water was added and extracted with EA. The combined organic phases were dried over anhydrous Na2SO4. After filtration and concentration, the residue was purified by MPLC. This resulted in 250 mg (53%) of 4-methyl-1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)-2,3-dihydro-1H-inden-1-ol as colorless oil. Finally, a solution of 4-methyl-1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)-2,3-dihydro-1H-inden-1-ol (100 mg, 0.29 mmol, 1.00 equiv) in HCOOH (10 mL), Palladium carbon (10 mg) was placed into a 100 mL round bottom flask. The resulting solution was heated to reflux for one overnight. The pH value of the solution was adjusted to 8 with aqueous sodium bicarbonate solution and extracted with EA. The combined organic phases were dried over anhydrous Na2SO4. After filtration and concentration, the residue was purified by MPLC. This resulted in 40 mg (67%) of 2-(4-methyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole as a white solid. LCMS (m/e) 199 (M+H); 1H NMR (300 MHz, CDC3) delta ppm 6.96-7.18 (m, 3H), 6.93 (s, 2H), 4.59 (t, J=8.1 Hz, 1H), 2.80-3.00 (m, 2H), 2.50-2.62 (m, 1H), 2.29 (s, 3H), 2.45-2.29 (s, 1H).
	With piperidine; pyridine; at 85℃; for 24h;	General procedure: A mixture of aromatic aldehydes (3.2 mmol), malonic acid (3.87 mmol), piperidine (0.387 mmol) was dissolved in pyridine and stirred on 85 for 24 h. The pyridine was removed at the vacuum. The reaction mixture was poured into water and washed with HCl. And the precipitate was filtered and washed with hexane for three times, and dried under vacuum to afford the cinnamic acids.
	With piperidine; pyridine; at 85℃; for 24h;	General procedure: A mixture of aromatic aldehydes (3.2 mmol), malonic acid (3.87 mmol), piperidine (0.387 mmol) was dissolved in pyridine and stirred on 85 C for 24 h. The pyridine was removed at the vacuum. The reaction mixture was poured into water and washed with HCl. And the precipitate was filtered and washed with hexane for three times, and dried under vacuum to afford the cinnamic acids.

References: [1]Patent: US2013/178457,2013,A1 .Location in patent: Paragraph 0173.
[2]Patent: WO2013/5168,2013,A2 .Location in patent: Page/Page column 32.
[3]Tetrahedron Letters,2011,vol. 52,p. 5371 - 5374.
[4]Journal of Organic Chemistry,1986,vol. 51,p. 1120 - 1123.
[5]Patent: WO2013/74892,2013,A1 .Location in patent: Page/Page column 39-40.
[6]Patent: US9125407,2015,B2 .Location in patent: Page/Page column 27; 28.
[7]Journal of the Chemical Society,1938,p. 357,362.
[8]Journal of the American Chemical Society,1950,vol. 72,p. 2530.
[9]Chemical Biology and Drug Design,2013,vol. 81,p. 275 - 283.
[10]Chemistry - A European Journal,2013,vol. 19,p. 3833 - 3837.
[11]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2876 - 2879.
[12]European Journal of Medicinal Chemistry,2014,vol. 81,p. 420 - 426.
[13]Organic and Biomolecular Chemistry,2017,vol. 15,p. 7272 - 7276.
[14]European Journal of Organic Chemistry,2020,vol. 2020,p. 878 - 883.

5
[ 939-57-1 ]
[ 118-90-1 ]

References: [1]Tetrahedron,1989,vol. 45,p. 2109 - 2126.

6
[ 939-57-1 ]
[ 87212-80-4 ]

References: [1]Tetrahedron Letters,1983,vol. 24,p. 2965 - 2968.

7
[ 939-57-1 ]
[ 84258-80-0 ]

References: [1]Chemistry of Heterocyclic Compounds,1982,vol. 18,p. 1246 - 1250.
Khimiya Geterotsiklicheskikh Soedinenii,1982,vol. 18,p. 1618 - 1622.

8
[ 939-57-1 ]
[ 529-20-4 ]

References: [1]Tetrahedron,1994,vol. 50,p. 10933 - 10944.
[2]Tetrahedron,1994,vol. 50,p. 10945 - 10954.

9
[ 939-57-1 ]
[ 529-20-4 ]
[ 298-12-4 ]

References: [1]Tetrahedron,1989,vol. 45,p. 2109 - 2126.

10
[ 70625-62-6 ]
[ 939-57-1 ]

References: [1]Chemistry of Heterocyclic Compounds,1982,vol. 18,p. 1246 - 1250.
Khimiya Geterotsiklicheskikh Soedinenii,1982,vol. 18,p. 1618 - 1622.

11
[ 75950-73-1 ]
[ 939-57-1 ]
[ 75950-74-2 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1983,p. 2399 - 2407.

12
2,3-Dibromo-3-o-tolyl-propionic acid [ No CAS ]
[ 939-57-1 ]

References: [1]Journal of the Indian Chemical Society,1988,vol. 65,p. 350 - 353.

13
[ 141-82-2 ]
[ 5469-00-1 ]
[ 939-57-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 1147 - 1156.

14
[ 939-57-1 ]
[ 83612-52-6 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In toluene; for 4h;Reflux;	In a 250 ml round bottom flask there were placed: 5 g frans-2-methylcinnamic acid, 30 ml toluene and 5 ml thionyl chloride (d=1.63 g/ml). The reaction mixture was refluxed for 4 hours, then solvents were evaporated under reduced pressure, 10 ml of toluene was added twice and evaporated.
	With thionyl chloride; In toluene; for 5h;Reflux;	General procedure: Syntheses of the tested compounds were carried out according to Scheme 1. The compounds were obtained by means of N-acylation of aminoalkanols by means of substituted cinnamic acid chlorides.20-22 4-Chloro, 4-methyl, and 2-methylcinnamic acid chlorides were obtained in the reactions of 4-chloro, 4-methyl, and 2-methylcinnamic acid with 10% excess of thionyl chloride in toluene. The reagents were refluxed for 5 h, then the solvent was evaporated under reduced pressure. In case of 4-Cl and 4-CH3-cinnamic acid chlorides the oily residues were crystallized from n-hexane what resulted in obtaining yellowish-white products, while 2-CH3-cinnamic acid chloride was not obtained in crystalline form and was used as a brown liquid.
	With thionyl chloride; In 1,2-dichloro-ethane; N,N-dimethyl-formamide;Reflux;	2-methylcinnamic acid (II-2,5 mmol) was dissolved in dichloroethane (10 mL), thionyl chloride (15 mmol) and DMF (1 drop). The mixture was heated to reflux for overnight. The next day, the reaction mixture was concentrated to dryness under reduced pressure to give cinnamoyl chloride (III-2) as an oily intermediate.

References: [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 2625 - 2631.
[2]Journal of the Chemical Society. Perkin transactions I,1997,p. 1147 - 1156.
[3]Journal of Heterocyclic Chemistry,2001,vol. 38,p. 961 - 964.
[4]Journal of Medicinal Chemistry,2006,vol. 49,p. 5333 - 5338.
[5]Tetrahedron Letters,2004,vol. 45,p. 6721 - 6723.
[6]Journal of Medicinal Chemistry,2007,vol. 50,p. 5176 - 5182.
[7]Journal of Medicinal Chemistry,2009,vol. 52,p. 1546 - 1552.
[8]Chemical Communications,2012,vol. 48,p. 4332 - 4334.
[9]Chemical Communications,2014,vol. 50,p. 4459 - 4461.
[10]Patent: WO2014/73994,2014,A2 .Location in patent: Page/Page column 7; 8.
[11]Journal of Chemical Research,2014,vol. 38,p. 542 - 545.
[12]Journal of the American Chemical Society,2016,vol. 138,p. 2146 - 2149.
[13]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 471 - 482.
[14]Organic and Biomolecular Chemistry,2017,vol. 15,p. 9804 - 9808.
[15]Patent: CN107383146,2017,A .Location in patent: Paragraph 0026.
[16]Chemical Communications,2019,vol. 55,p. 6118 - 6121.

15
[ 24393-48-4 ]
[ 939-57-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 2625 - 2631.
[2]Synthetic Communications,2002,vol. 32,p. 195 - 201.
[3]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 747 - 749.
[4]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 747 - 749.
[5]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 747 - 749.

16
[ 939-57-1 ]
[ 119193-19-0 ]
RTI 5989-25 [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1980 - 1990.

17
[ 939-57-1 ]
2-(1-amino-ethyl)-5-methyl-thieno[2,3-d][1,3]oxazin-4-one; compound with trifluoro-acetic acid [ No CAS ]
N-[1-(5-methyl-4-oxo-4H-thieno[2,3-d][1,3]oxazin-2-yl)-ethyl]-3-o-tolyl-acrylamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 443 - 448.

Yield	Reaction Conditions	Operation in experiment
90%		EXAMPLE 3 o-Methylcinnamic acid 292 g (1.08 moles) of ethyl 2-chloro-2-(o-methylbenzyl)-acetoacetate were added dropwise to 4.85 moles of 25% strength aqueous NaOH solution in the course of 1 hour. The refluxed mixture was then stirred for a further 6 hours. The reaction solution was reacted twice by shaking with toluene and then acidified with semiconcentrated hydrochloric acid, and the precipitate which had separated out was filtered off under suction. It was rinsed with water and toluene and dried in a drying oven. 157 g (90% of the theoretical yield) of o-methylcinnamic acid of melting point 176 to 177 C. were obtained.
90%	With piperidine; pyridine; at 20℃;Inert atmosphere;	General procedure: Preparation example 9: (E)-3-(2-f luorophenyl )-acryl ic acid Piper idi ne (247mg, 2.90inmol) was added to a stri'ied solution of ma Ionic acid (3.1g, 29.00mmol) and 2-f luoroaldehyde (3g, 24.17mmol) in pyridine at room temperature under N2 condition. The solution was cooled to room temperature, then quenched with HC1 solution. The residue was treated with EA and 0. The organic layer was separated and the aqueous layer was extracted further with EA. The combined extracts were washed with brine. The organic layer was dried over Na2S0 , filtered and concentrated. The crude compound was purified by a silica gel column to produce the title compound (3.66g, 70-90%). NMR (400MHz, CDC 13 ) delta 6.60(cl, J=16.0, 1H) , 7.24~7.50(m, 3H), 7.66(d, J=16.0, 1H), 7.84(t, J=8.0, 1H)
16.5 g (35%)		Trans-2-methyl-cinnamic acid See H. Zimmer, D. C. Armbruster, and L. J. Trauth, J. Heterocyclic Chem., 3:232 (1966). A mixture of 35.1 g (0.29 mol) of o-tolualdehyde, 47.6 g (0.46 mol) of acetic anhydride, and 18 g (0.174 mol) of fused and pulverized potassium acetate was heated at 155-160 for 15 minutes and then at 165-170 for 12 hours. The mixture was diluted with 1 liter of ice water and steam distilled to remove excess aldehyde. On cooling, a yellow solid formed. The solid was collected, washed with water, dissolved in chloroform, treated with charcoal, and filtered. The filtrate was concentrated and the residue was recrystallized from ethanol/ether to give 16.5 g (35%) of trans-2-methylcinnamic acid; mp 173-175.

1.5 g

With piperidine; pyridine; at 20℃;Inert atmosphere;

General procedure: Piperidine (247mg, 2.90mmol) was added to a striied solution of malonic acid (3.1g, 29.00mmol) and 2-fluoroaldehyde (3g, 24.17mmol) in pyridine at room temperature under N2 condition. The solution was cooled to room temperature, then quenched with HCI solution. The residue was treated with EA and H20. The organic layer was separated and the aqueous layer was extracted further with EA. The combined extracts were washed with brine. The organic layer was dried over Na2S04, filtered and concentrated. The crude compound was purified by a silica gel column to produce the title compound (3.66g, 70~90%). 1H NMR(400MHz, CDCI3) 66.60(d, J=16.0, 1H), 7.24~7.50(m, 3H), 7.66(d, J=16.0, 1H), 7.84(t, J=8.0, 1H

20
[ 13331-23-2 ]
[ 342777-09-7 ]
[ 939-57-1 ]
(E)-3-(2-Furan-2-ylmethyl-phenyl)-acrylic acid [ No CAS ]