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24393-56-4 Usage

Chemical Properties

White crystalline, soluble in methanol, ethanol, DMSO and other organic solvents, derived from cinnamon.

Uses

Ethyl 4-methoxycinnamate is an derivative of 4-methoxycinnamic acid, an antihyperglycemic/hypoglycemic agent that works by stimulating insulin secretion from pancreas and could be developed into a new potential for therapeutic agent used in type 2 diabetic patients.

Preparation

Ethyl 4-methoxycinnamate synthesis: 4-Methoxycinnamic Acid (0.60 g, 3.36 mmol) was dissolved in 10 mL of dry N,N-dimethylformamide (DMF) in a 25-mL, roundbottomed flask. Cesium carbonate (1.65 g, 5.06 mmol) was added followed by iodoethane (1.0 mL, 12.5 mmol). The flask was capped (rubber septum) and the heterogeneous mixture stirred vigorously at 50 °C for one hour. After this time, HCl (1.0 M, 4.0 mL) was added to quench the reaction. The liquid was decanted from any remaining solid and extracted with 3 : 1 hexanes/ethyl acetate (2 x 10 mL). The organic layer was washed with brine (20 mL), dried with MgSO4, filtered, and solvent removed. The remaining oil solidified on standing to form colorless prisms.Synthesis of ethyl 4-methoxycinnamate

General Description

Ethyl p-methoxycinnamate (EPMC) is a natural product found in K. galanga and C. zedoaria extracts with anti-inflammatory, antiangiogenic, antifungal, larvicidal, and analgesic activities. It inhibits COX-1 and COX-2 in vitro (IC50s = 1.12 and 0.83 μM, respectively) and reduces IL-1 and TNF-α production in vivo. EPMC inhibits granuloma tissue formation and acts as an analgesic, delaying tail flick time, in a dose-dependent manner in rats. It inhibits blood vessel growth in rat aortic explants (IC50 = 91.9 μg/ml). EPMC (<10 μg/ml) also reduces growth of T. rubrum, A. niger, S. cerevisiae, and E. floccosum and is larvicidal (LC50 = 53.64 ppm) against Ae. aegypti.

Check Digit Verification of cas no

The CAS Registry Mumber 24393-56-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,4,3,9 and 3 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 24393-56:
(7*2)+(6*4)+(5*3)+(4*9)+(3*3)+(2*5)+(1*6)=114
114 % 10 = 4
So 24393-56-4 is a valid CAS Registry Number.
InChI:InChI=1S/C12H14O3/c1-3-15-12(13)9-6-10-4-7-11(14-2)8-5-10/h4-9H,3H2,1-2H3/b9-6+

24393-56-4 Well-known Company Product Price

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  • TCI America

  • (M1204)  Ethyl 4-Methoxycinnamate  >98.0%(GC)

  • 24393-56-4

  • 5g

  • 760.00CNY

  • Detail
  • TCI America

  • (M1204)  Ethyl 4-Methoxycinnamate  >98.0%(GC)

  • 24393-56-4

  • 25g

  • 1,990.00CNY

  • Detail
  • Sigma-Aldrich

  • (42479)  Ethyl trans-4-methoxycinnamate  analytical standard

  • 24393-56-4

  • 42479-10MG

  • 1,944.54CNY

  • Detail

24393-56-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl 4-methoxycinnamate

1.2 Other means of identification

Product number -
Other names 3-(4-Methoxyphenyl)acrylic Acid Ethyl Ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:24393-56-4 SDS

24393-56-4Synthetic route

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
In dichloromethane at 22℃; for 16h; Wittig reaction;100%
In dichloromethane at 20 - 25℃; Inert atmosphere;96%
In dichloromethane at 20℃; for 16h; Inert atmosphere;77%
ethyl potassium malonate
6148-64-7

ethyl potassium malonate

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With acetic acid; piperidine; dmap In N,N-dimethyl-formamide at 10 - 20℃; for 24h; Product distribution / selectivity;100%
With piperidine; dmap; acetic acid In N,N-dimethyl-formamide at 20℃; for 72h;98%
With piperidine; dmap; acetic acid In N,N-dimethyl-formamide at 10 - 25℃; Knoevenagel reaction;97%
With hydrogenchloride; piperidine; dmap In diethyl ether; N,N-dimethyl-formamide at 10 - 20℃; for 24h; Product distribution / selectivity;96%
1-ethoxy-1-(trimethylsiloxy)-2-(trimethylsilyl)ethene
65946-56-7

1-ethoxy-1-(trimethylsiloxy)-2-(trimethylsilyl)ethene

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With tetrabutylammonium acetate In dichloromethane at 0℃; for 1h;100%
With 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In acetonitrile at 0 - 20℃; Peterson Olefination; stereoselective reaction;82%
ethanol
64-17-5

ethanol

(E)-3-(4-methoxyphenyl)acrylic acid
943-89-5

(E)-3-(4-methoxyphenyl)acrylic acid

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With sulfuric acid for 16h; Heating;99%
With sulfuric acid for 12h; Reflux; Inert atmosphere;99%
With sulfuric acid at 90℃; for 16h;96%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene at 25℃; for 24h; Horner-Wadsworth-Emmons reaction; Inert atmosphere; neat (no solvent); optical yield given as %de; stereoselective reaction;99%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 30℃; for 4h; Glovebox;99%
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; for 2h; Horner-Wadsworth-Emmons olefination; Inert atmosphere; Neat (no solvent); stereoselective reaction;95%
para-iodoanisole
696-62-8

para-iodoanisole

ethyl acrylate
140-88-5

ethyl acrylate

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate at 130℃; for 16h; Heck olefination;99%
With potassium carbonate; Pd on 3-[(2-aminoethyl)amino]propyl-functionalized silica In N,N-dimethyl acetamide at 130℃; for 12h; Heck reaction;99%
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 20℃; for 24h; Heck Reaction; Schlenk technique; Inert atmosphere; Cooling with liquid nitrogen; Irradiation;99%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide at 25℃; Doebner-Knoevenagel reaction;99%
With dmap In N,N-dimethyl-formamide at 25℃; Knoevenagel reaction;99%
piperidine; dmap In N,N-dimethyl-formamide at 10 - 20℃; for 24h; Product distribution / selectivity;99%
With poly{styrene-co-[4-(N-methyl-N-vinylbenzyl-amino)pyridine]-co-[1-phenyl-3-(4-vinylbenzyl)piperazine]} In N,N-dimethyl-formamide at 50℃; decarboxylative Doebner-Knoevenagel condensation reaction; optical yield given as %de;97%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl bromoacetate
105-36-2

ethyl bromoacetate

A

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

B

(Z)-ethyl 3-(4-methoxyphenyl)acrylate
51507-22-3

(Z)-ethyl 3-(4-methoxyphenyl)acrylate

Conditions
ConditionsYield
With potassium carbonate In ethanol Wittig Olefination; Milling; diastereoselective reaction;A 98%
B n/a
With tributylphosphine; tetrakis(triphenylphosphine) palladium(0) at 110℃; for 24h; Yield given. Yields of byproduct given;
With sodium hydrogencarbonate; triphenylphosphine at 20℃; for 2h; Wittig reaction; Title compound not separated from byproducts.;
(carbethoxymethyl)triphenylphosphonium bromide
1530-45-6

(carbethoxymethyl)triphenylphosphonium bromide

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With potassium carbonate In dichloromethane; water at 25℃; Wittig reaction; Sonication; stereoselective reaction;98%
With triethylamine In dichloromethane at 20℃; for 16h; Inert atmosphere; Schlenk technique;
2Br(1-)*C26H32NO2P(2+)

2Br(1-)*C26H32NO2P(2+)

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 40℃; for 50h; Wittig reaction; Inert atmosphere; optical yield given as %de; diastereoselective reaction;98%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With Fe(TCP)Cl; polyethylene supported arsine; polymethylhydrosiloxane In toluene at 110℃; for 12h; Wittig type reaction; Inert atmosphere; optical yield given as %de; stereoselective reaction;97%
tris(triphenylphosphine)ruthenium(II) chloride In 1,2-dichloro-ethane at 50℃; for 12h;92%
With sodium disulfite; triphenyl-arsane; chloro[tetra(p-chlorophenyl)porphyrinato]iron(III) In water; toluene at 80℃; for 8h;81%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

ethyl acrylate
140-88-5

ethyl acrylate

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With PEG-OCOCH2CH2CO2CH2CH2-supported 3-methyl-imidazolium*Cl; potassium carbonate; palladium diacetate at 140℃; for 10h; Heck reaction;96%
With potassium phosphate; tetrabutylammomium bromide; [PdCl{[η5-C5H5)]Fe[(η5-C5H3)C(CH3)=NC12H25]}]2 In N,N-dimethyl-formamide at 140℃; for 12h; Heck coupling;95%
With C37H38BrClFeN3Pd; potassium acetate In N,N-dimethyl acetamide at 150℃; for 12h; Heck reaction; Inert atmosphere; regioselective reaction;93%
5-(4-methoxybenzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione
15795-54-7

5-(4-methoxybenzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione

ethanol
64-17-5

ethanol

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
Stage #1: 5-(4-methoxybenzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione; ethanol With iron(III) chloride hexahydrate In nitromethane for 0.25h; Microwave irradiation;
Stage #2: With piperidine In nitromethane for 0.25h; Microwave irradiation; stereoselective reaction;
96%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

A

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

B

(Z)-ethyl 3-(4-methoxyphenyl)acrylate
51507-22-3

(Z)-ethyl 3-(4-methoxyphenyl)acrylate

Conditions
ConditionsYield
With triphenylphosphine In toluene at 80℃; for 6h; Inert atmosphere; optical yield given as %de; stereoselective reaction;A 95%
B n/a
With 5,10,15,20-tetraphenyl porphyrinato iron hydroxide; lithium bromide; phosphorous acid trimethyl ester In 1,4-dioxane at 85℃; for 18h; Wittig olefination;A 58%
B 1%
With triphenylphosphine; MoO2(S2CNEt2)2 In benzene at 80℃; for 5h; Yield given. Yields of byproduct given;
4-methoxybenzenediazonium tetrafluoroborate
459-64-3

4-methoxybenzenediazonium tetrafluoroborate

ethyl acrylate
140-88-5

ethyl acrylate

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With palladium diacetate In water at 20℃; for 16h; Heck Reaction;95%
With 3-benzyl-1-(2-hydroxy-2-phenylethyl)imidazolium chloride; palladium diacetate In ethanol at 36℃; for 3h; Heck-Matsuda reaction;92%
[(1,3-dimesitylimidazol-2-ylidene)(naphthoquinone)Pd(0)]2 In methanol at 50℃; for 1h; Heck reaction;91%
(IMes)Pd(NQ) In ethanol at 50℃; for 1h; Conversion of starting material; Heck Reaction;90%
With palladium(II) carboxymethylcellulose In water at 20℃; for 8h;81%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl bromoacetate
105-36-2

ethyl bromoacetate

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
Stage #1: ethyl bromoacetate With triphenyl phosphite; PEG-Te-Bu In toluene at 80℃; for 0.166667h;
Stage #2: With potassium carbonate In toluene for 0.0166667h;
Stage #3: 4-methoxy-benzaldehyde In toluene for 43h; Wittig-type olefination; Further stages.;
94%
With triphenyl phosphite; poly(ethylene glycol) di(2-(n-butyltelluro)ethyl) ether; potassium carbonate In toluene at 80℃;94%
With triphenyl phosphite; potassium carbonate; (BrBu2Te)2O In toluene at 80℃; for 72h; Wittig-type olefination;94%
ketene diethyl acetal
2678-54-8

ketene diethyl acetal

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With (2,4,5-trifluorophenyl)boronic acid In tert-butyl methyl ether at 50℃; for 14h;94%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With manganese In tetrahydrofuran for 3h; Heating;92%
With manganese In tetrahydrofuran for 3h; Reflux; Inert atmosphere; optical yield given as %de; stereoselective reaction;92%
4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

ethyl acrylate
140-88-5

ethyl acrylate

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 8h; Heck Reaction;91%
With C34H29BrCl2OP2Pd; potassium carbonate In water; N,N-dimethyl-formamide at 110℃; for 6h;66%
With C37H30Cl2OP2Pd; caesium carbonate In N,N-dimethyl acetamide; water at 110℃; for 4.5h; Heck Reaction; Green chemistry;61%
ethyl acrylate
140-88-5

ethyl acrylate

4-methoxybenzenediazonium o-benzenedisulfonimide

4-methoxybenzenediazonium o-benzenedisulfonimide

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With (triphenylphosphine)gold(I) chloride; calcium carbonate In acetonitrile at 35℃; for 5h; Inert atmosphere;91%
palladium diacetate In ethanol at 70℃; for 0.666667h; Heck arylation;84%
2Br(1-)*C28H34NO2P(2+)

2Br(1-)*C28H34NO2P(2+)

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 40℃; for 24h; Wittig reaction; Inert atmosphere; optical yield given as %de; diastereoselective reaction;91%
ethanol
64-17-5

ethanol

2-bromo-3-(4-methoxyphenyl)prop-2-enal
13532-16-6

2-bromo-3-(4-methoxyphenyl)prop-2-enal

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,3-bis(mesityl)imidazolium chloride In tetrahydrofuran at 20℃; Inert atmosphere; optical yield given as %de; stereoselective reaction;91%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl 4,4,4-trifluoroacetoacetate
372-31-6

ethyl 4,4,4-trifluoroacetoacetate

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With piperidine; aluminum oxide for 0.266667h; Microwave irradiation;89%
With piperidine In dichloromethane at 20℃; for 7h; stereoselective reaction;84%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl acetate
141-78-6

ethyl acetate

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With sodium hydride at 10 - 20℃; for 0.583333h;87%
With trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine Mukaiyama Aldol Addition; Inert atmosphere;70%
With P(i-PrNCH2CH2)3N at 50℃; for 6h;60%
With sodium
With sodium
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

A

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

B

(Z)-ethyl 3-(4-methoxyphenyl)acrylate
51507-22-3

(Z)-ethyl 3-(4-methoxyphenyl)acrylate

Conditions
ConditionsYield
Stage #1: 4-Methoxybenzyl alcohol With 1,10-Phenanthroline; potassium tert-butylate; copper(l) chloride In fluorobenzene at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With 1-methyl-1H-imidazole; di-tert-butyl-diazodicarboxylate; oxygen In fluorobenzene Reflux;
Stage #3: diazoacetic acid ethyl ester With triphenylphosphine In fluorobenzene Inert atmosphere; optical yield given as %de; stereoselective reaction;
A 87%
B n/a
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

ethyl acrylate
140-88-5

ethyl acrylate

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With C48H40N4O4Pd2(4+); acetic acid; p-benzoquinone In water at 20℃; for 12h; Heck Reaction; Inert atmosphere;87%
With pyrrolidine; 5%-palladium/activated carbon; tetrabutylammomium bromide; oxygen In 1-methyl-pyrrolidin-2-one at 80℃; under 2587.76 Torr; for 12h; Heck Reaction;85%
With [2,2]bipyridinyl; oxygen; palladium diacetate In N,N-dimethyl-formamide at 20℃; Heck reaction;65 %Spectr.
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

A

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

B

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester; 4-methoxy-benzaldehyde With potassium carbonate for 6h; Horner-Wadsworth-Emmons olefination; Neat (no solvent); high-speed ball milling;
Stage #2: With Oxone for 12h; Neat (no solvent); high-speed ball milling; optical yield given as %de; diastereoselective reaction;
A 87%
B n/a
4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With C34H37N4O6Ru2(1+)*Cl(1-); potassium hydroxide In toluene at 70℃; for 6h; Wittig Olefination; Schlenk technique; Inert atmosphere;86%
With oxygen; caesium carbonate In toluene at 50℃; under 760.051 Torr; for 24h; Green chemistry;85%
With dipyridinium dichromate In dichloromethane at 20℃; for 24h; Wittig Olefination;81%
With hollandite In toluene at 110℃; for 4h; Catalytic behavior; Wittig Olefination; diastereoselective reaction;80%
With aluminum (III) chloride; Oxone In water at 20℃; for 3h; Wittig reaction; stereoselective reaction;55%
n-propyl acrylate
925-60-0

n-propyl acrylate

para-iodoanisole
696-62-8

para-iodoanisole

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 75℃; for 7h; Heck Reaction; Green chemistry;86%
E-1-(4'-methoxyphenyl)prop-1-ene
4180-23-8

E-1-(4'-methoxyphenyl)prop-1-ene

ethyl acrylate
140-88-5

ethyl acrylate

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With Hoveyda-Grubbs catalyst first generation In 1,2-dichloro-ethane at 70℃; Cross Metathesis; Schlenk technique; Inert atmosphere; Glovebox;85%
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

ethyl trans-3-(4-methoxyphenyl)oxirane-2-carboxylate

ethyl trans-3-(4-methoxyphenyl)oxirane-2-carboxylate

Conditions
ConditionsYield
With Oxone; potassium carbonate; acetic acid; rac-2-F-2,5-(Me)2-5-(2-fluoroisopropyl)-cyclohexanone In 1,4-dioxane; water at 20℃; for 6h; pH=8.5 - 9;100%
With Oxone; sodium hydrogencarbonate In water; acetone at 20℃; for 24h;
With Oxone; sodium hydrogencarbonate In water; acetone; acetonitrile at 0℃; for 5h;
3,4-Dimethylphenol
95-65-8

3,4-Dimethylphenol

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

6,7-dimethyl-4-(4'-methoxyphenyl)-3,4-dihydrocoumarin
85903-43-1

6,7-dimethyl-4-(4'-methoxyphenyl)-3,4-dihydrocoumarin

Conditions
ConditionsYield
With trifluoroacetic acid at 20℃; for 24h;100%
Sesamol
533-31-3

Sesamol

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

8-(4-methoxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]-chromen-6-one
267901-33-7

8-(4-methoxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]-chromen-6-one

Conditions
ConditionsYield
With trifluoroacetic acid at 20℃; for 24h;100%
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

β-naphthol
135-19-3

β-naphthol

1,2-dihydro-1-(4-methoxyphenyl)-3H-naphtho[2,1-b]pyran-3-one

1,2-dihydro-1-(4-methoxyphenyl)-3H-naphtho[2,1-b]pyran-3-one

Conditions
ConditionsYield
With trifluoroacetic acid at 20℃; for 24h;100%
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

ethyl 3-(4-methoxyphenyl)propanoate
22767-72-2

ethyl 3-(4-methoxyphenyl)propanoate

Conditions
ConditionsYield
With 0.42C23H20N4O4*2Cl(1-)*Zn(2+)*10.16H2O*0.58Pd(2+)*0.58C23H20N4O4(1-); hydrogen In tetrahydrofuran at 20℃; under 760.051 Torr; for 1h;99%
With hydrogen; platinum(IV) oxide In various solvent(s) at 25℃; for 2h;93%
With ethanol; nickel at 80 - 90℃; under 73550.8 Torr; Hydrogenation;
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester
157019-58-4

2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester

Conditions
ConditionsYield
With bromine99%
With bromine In tetrachloromethane Heating;
With bromine In dichloromethane at 0℃;
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

(E)-p-methoxy-cinnamyl alcohol
53484-50-7

(E)-p-methoxy-cinnamyl alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at -10 - 20℃; for 1h;98%
With diisobutylaluminium hydride In dichloromethane; toluene at -78℃; for 1.5h;94%
With diisobutylaluminium hydride In dichloromethane at -78 - 20℃; for 2h; Inert atmosphere;90%
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

3,5-Dimethylphenol
108-68-9

3,5-Dimethylphenol

5,7-dimethyl-4-(4-methoxyphenyl)-3,4-dihydrobenzopyran-2-one
85903-47-5

5,7-dimethyl-4-(4-methoxyphenyl)-3,4-dihydrobenzopyran-2-one

Conditions
ConditionsYield
With trifluoroacetic acid at 20℃; for 24h;98%
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

ethyl 3-(4-methoxyphenyl)-3-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)-propionate

ethyl 3-(4-methoxyphenyl)-3-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)-propionate

Conditions
ConditionsYield
With methanol; sodium t-butanolate; bis[2-(diphenylphosphino)phenyl] ether; copper(l) chloride In tetrahydrofuran at 20℃; for 3h;98%
With NaOt-Bu; (+)-[Rh((S,S)-Phebox-i-Pr)OAc2(H2O)] In toluene under Ar; mixt. of MeOC6H4CHCHC(O)OEt (0.5 mmol), B2pin2 (0.6 mmol), NaOt-Bu (0.025-0.029 mmol) and Rh complex catalyst (1 mol%) stirred at 80°C for 0.5 h; chromd. (SiO2 column, hexane/ehtyl acetate eluent); 83% ee;91%
With NaOt-Bu; [rhodium(III)(bis(COCH2CH(s-Bu)N)phenyl)(OAc)2(H2O)] In toluene under Ar; mixt. of MeOC6H4CHCHC(O)OEt (0.5 mmol), B2pin2 (0.6 mmol), NaOt-Bu (0.025-0.029 mmol) and Rh complex catalyst (1 mol%) stirred at 80°C for 0.5 h; chromd. (SiO2 column, hexane/ehtyl acetate eluent); 94% ee;90%
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

(E)-3-(4-methoxyphenyl)acrylic acid
943-89-5

(E)-3-(4-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran; water at 25℃; for 24h;97%
With sodium hydroxide In ethanol; water at 20℃; for 16h;80%
With lithium hydroxide monohydrate In methanol for 2h; Reflux;72%
ethylenebis(triphenylphosphine)platinum(0)
12120-15-9

ethylenebis(triphenylphosphine)platinum(0)

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

bis(triphenylphosphine)-(η2-ethyl 4-methoxycinnamate)platinum(0)

bis(triphenylphosphine)-(η2-ethyl 4-methoxycinnamate)platinum(0)

Conditions
ConditionsYield
In benzene for 1h; Inert atmosphere;97%
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

isoprene
78-79-5

isoprene

(±)-ethyl (1S,2S)-4'-methoxy-4-methyl-1,2,3,6-tetrahydro-[1,1'-biphenyl]-2-carboxylate

(±)-ethyl (1S,2S)-4'-methoxy-4-methyl-1,2,3,6-tetrahydro-[1,1'-biphenyl]-2-carboxylate

Conditions
ConditionsYield
With iron(III) chloride In acetonitrile at 0℃; for 24h; regioselective reaction;96%
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

ethyl 2,3-dihydroxy-3-(4-methoxyphenyl)propionate
253350-07-1

ethyl 2,3-dihydroxy-3-(4-methoxyphenyl)propionate

Conditions
ConditionsYield
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In various solvent(s) at 25℃; for 2h;95%
With chiral 3,6-bis(9-O-dihydroquinyl)pyridazine(thioethanol) immobilized on chloropropyl-silica gel; potassium carbonate; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 20℃; for 36h;69%
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

ethyl (2S,3R)-2,3-dihydroxy-3-(4-methoxyphenyl)propanoate
159848-77-8

ethyl (2S,3R)-2,3-dihydroxy-3-(4-methoxyphenyl)propanoate

Conditions
ConditionsYield
With osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine In water; tert-butyl alcohol at 0℃; for 16h;94%
With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; 4-methylmorpholine N-oxide; polyaniline-supported Os In water; acetone; acetonitrile at 20℃; for 12h; Sharpless asymmetric dihydroxylation;93%
With (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; 4-methylmorpholine N-oxide; Mg(1-x)Al(x)(OH)2(Cl)2*zH2O-OsO4 In water; tert-butyl alcohol at 20℃; for 12h;93%

24393-56-4Relevant articles and documents

Tuning and enhancement of the Mizoroki-Heck reaction using polarized Pd nanocomposite carbon aerogels

Martín, Laura,Molins, Elies,Vallribera, Adelina

, p. 10208 - 10212 (2016)

The application of a positive electric field on a Pd(0)-carbon aerogel nanocomposite enhances the reaction rate of the Mizoroki-Heck reaction. By contrast, when a negative potential is employed the reaction is inhibited. On the other hand, chronoamperometry measurements have revealed the polarizing current intensity as an indirect measure of the reaction evolution. The cationic nature of the reaction intermediates was unambiguously confirmed and a polar mechanism has been finally proposed.

Barium Hydroxide as Catalyst in Organic Reactions; V. Application in the Horner Reaction under Solid-Liquid Phase-Transfer Conditions

Sinisterra, J. V.,Mouloungui, Z.,Delmas, M.,Gaset, A.

, p. 1097 - 1100 (1985)

A new application of a barium hydroxide catalyst for the Horner reaction is described.The scope of the synthetic method is shown; furthermore, the yields are higher and the reaction times shorter than those previously reported for similar experimental conditions (solid-liquid).Ethyl 3-(1'-pyrenyl)-acrylate and the 3-(1'-pyrenyl)-acrylonitrile are described for the first time.

Asymmetric synthesis of piperidines using the nitro-Mannich reaction☆

Anderson, James C.,Bouvier-Israel, Eva,Rundell, Christopher D.,Zhang, Xiangyu

, (2020/12/21)

A method for the synthesis of functionalized piperidines containing 3 contiguous stereocentres in the 2-,3- and 4- positions uses a diastereoselective nitro-Mannich to control stereochemistry. The nitro-Mannich reaction between a β-aryl/heteroaryl substituted nitroalkanes and glyoxylate imine provides β-nitro-amines with good selectivity (70:30 to >95:5) for the syn, anti-diastereoisomers. Reductive cyclisation with BF3.OEt2 and Et3SiH gave, after purification, stereochemically pure piperidines in 19–57% yield for ten examples with different 4-aryl/heteroaryl substituents.

Pd/Cu-Free Cobalt-Catalyzed Suzuki and Heck Using Green Bio-Magnetic Hybrid and DFT-Based Theoretical Study

Hajipour, Abdol R.,Khorsandi, Zahra,Ahmadi, Mehnoosh,Jouypazadeh, Hamidreza,Mohammadi, Bahareh,Farrokhpour, Hossein

, p. 2842 - 2850 (2021/02/01)

Abstract: Several highly efficient and magnetically recyclable cobalt catalytic systems were prepared using magnetic chitosan and some safe and available organic compounds (Co-ligand@MNPs/Ch). The structure of these nanocomposites was confirmed by various physicochemical techniques such as FT-IR, XRD, TGA, VSM, TEM, SEM, CHNS and ICP-OES. These nano composites exhibit remarkable catalytic efficiency for Suzuki and Heck cross-coupling reactions in mild and green reaction conditions. The facile accessibility of starting materials, possible performance in air and eco-friendly conditions are merits of our catalysts. In addition, to describe and go insight to role and effect of ligands present in these catalysts, electrostatic interactions, density functional theory (DFT) model in molecular method were employed. Graphic Abstract: [Figure not available: see fulltext.]

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