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Ethyl 4-Hydroxyhydrocinnamate

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Ethyl 4-Hydroxyhydrocinnamate Basic information
Product Name:Ethyl 4-Hydroxyhydrocinnamate
Synonyms:Ethyl p-hydroxyphenylpropionate;Ethyl 3-(4-hydroxyphenyl)propionate, 4-(3-Ethoxy-3-oxoprop-1-yl)phenol;ethyl 4-hydroxyhydrocinnamate;ETHYL P-HYDROXYHYDROCINNAMATE;3-(4-HYDROXY-PHENYL)-PROPIONIC ACID ETHYL ESTER;Ethyl 3-(4-hydroxyphenyl)propanoate, 95+%;Ethyl 3-(4-hydroxyphenyl)propanoate 95%;Ethyl 3-(4-hydroxyphenyl)propionate
CAS:23795-02-0
MF:C11H14O3
MW:194.23
EINECS:
Product Categories:Aromatic Cinnamic Acids, Esters and Derivatives
Mol File:23795-02-0.mol
Ethyl 4-Hydroxyhydrocinnamate Structure
Ethyl 4-Hydroxyhydrocinnamate Chemical Properties
Melting point 40 °C
Boiling point 140 °C(Press: 0.2 Torr)
density 1.108
storage temp. Inert atmosphere,Room Temperature
form low melting solid / colourless liquid
pka9.99±0.15(Predicted)
color White
CAS DataBase Reference23795-02-0(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Safety Statements 24/25
Hazard Note Irritant
HS Code 2916399090
MSDS Information
Ethyl 4-Hydroxyhydrocinnamate Usage And Synthesis
Synthesis
Ethanol

64-17-5

3-(4-Hydroxyphenyl)propionic acid

501-97-3

Ethyl 4-Hydroxyhydrocinnamate

23795-02-0

GENERAL METHODS: Ethanol (1.0 mL) was added to a suspension of 3-(4-hydroxyphenyl)propanoic acid (0.05 mmol) and trimethylchlorosilane (TMCS, 0.1 mmol), and the reaction mixture was stirred at 25 °C for 24 h. The reaction was completed by evaporation of the solvent. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure to afford ethyl 3-(4-hydroxyphenyl)propionate (1b) in quantitative yield without further purification. The product was an oil; 1H NMR (400 MHz, CDCl3): δ 1.13 (3H, m, CH3), 2.82 (2H, m, CH2), 2.88 (2H, m, CH2), 4.00 (2H, m, OCH2), 6.75 (2H, m, Ph-H), 7.06 (2H, m, Ph-H); 13C NMR (50 MHz, CDCl3): δ 14.20 (CH3), 30.12 (CH2), 35.10 (CH2), 60.10 (CH2), 115.45 (2CH), 129.48 (2CH), 131.75 (C), 155.43 (C), 172.10 (CO); MS (EI): m/z 266; elemental analysis: Calculated values C, 68.02; H, 7.27; O, 24.71, measured values C, 68.0; H, 7.26; O, 24.68.

References[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5345 - 5351
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 7, p. 1495 - 1503
[3] Tetrahedron Letters, 2010, vol. 51, # 44, p. 5753 - 5756
[4] Molecules, 2018, vol. 23, # 2,
[5] Patent: US2010/298422, 2010, A1. Location in patent: Page/Page column 18
Ethyl 4-Hydroxyhydrocinnamate Preparation Products And Raw materials
Raw materialsEthanol-->2-Propenoic acid, 3-(4-hydroxyphenyl)-, ethyl ester, (Z)--->3-(4-Hydroxyphenyl)propionic acid
Preparation ProductsMethyl 3-(4-hydroxyphenyl)propionate
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