Methyl homoveratrate

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Methyl homoveratrate Basic information
Product Name:Methyl homoveratrate
Synonyms:METHYL 3,4-DIMETHOXYPHENYL ACETATE;VERATRYLACETIC ACID METHYL ESTER;Acetic acid, (3,4-dimethoxyphenyl)-, methyl ester;Homovanillic acid di-methyl derivative;Homoveratric acid, methyl ester;Methyl ester of 3,4-Dimethoxyphenylacetic acid;Phenylacetic acid, 3,4-dimethoxy, methyl ester;2-(3,4-Dimethoxyphenyl)acetic acid methyl ester
CAS:15964-79-1
MF:C11H14O4
MW:210.23
EINECS:240-100-3
Product Categories:Catechol Derivatives;Aromatic Esters
Mol File:15964-79-1.mol
Methyl homoveratrate Structure
Methyl homoveratrate Chemical Properties
Boiling point 175℃ (15 Torr)
density 1.105±0.06 g/cm3 (20 ºC 760 Torr)
refractive index 1.5253 (23℃)
Fp 121.6±23.2℃
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Slightly), Methanol (Slightly)
form Oil
color Colourless
EPA Substance Registry SystemBenzeneacetic acid, 3,4-dimethoxy-, methyl ester (15964-79-1)
Safety Information
TSCA TSCA listed
MSDS Information
Methyl homoveratrate Usage And Synthesis
UsesMethyl Homoveratrate can be used as entry inhibitors against H5N1.
Synthesis
Methanol

67-56-1

(3,4-Dimethoxyphenyl)acetic acid

93-40-3

METHYL HOMOVERATRATE

15964-79-1

General procedure for the synthesis of methyl 3,4-dimethoxyphenylacetate from methanol and 3,4-dimethoxyphenylacetic acid: 3,4-dimethoxyphenylacetic acid (25.0 g, 127.4 mmol) was dissolved in methanol (100 mL) in a 500 mL round-bottomed flask and a catalytic amount of sulfuric acid (about 10 drops) was added. The reaction mixture was stirred overnight under reflux conditions. After completion of the reaction, it was cooled to room temperature and methanol was removed by distillation under reduced pressure at 40 °C. The crude product was dissolved in dichloromethane (250 mL), washed sequentially with water (5 x 20 mL) and saturated saline (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give methyl 3,4-dimethoxyphenylacetate (25.77 g, 96% yield) as an orange oil. Molecular weight: 210.23; yield: 96%; Rf value: 0.25 (cyclohexane:ethyl acetate=3:1). 1H-NMR (CDCl3, δ): 3.56 (s, 2H, CH2), 3.70 (s, 3H, CH3), 3.87 (s, 3H, OCH3), 3.88 (s, 3H, OCH3), 6.82-6.83 (m , 3H, ArH).13C-NMR (CDCl3, δ): 40.6, 51.9, 55.8 (2 × C), 111.2, 112.4, 121.4, 126.4, 148.2, 148.9, 172.2.MS-ESI m/z (% relative abundance): 233.2 ([M+Na]+, 3), 151.1 ( 100).

References[1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 1, p. 85 - 90
[2] Tetrahedron, 2007, vol. 63, # 46, p. 11377 - 11385
[3] Tetrahedron, 2013, vol. 69, # 42, p. 8914 - 8920
[4] Patent: US2012/214837, 2012, A1. Location in patent: Page/Page column 23-24
[5] Journal of Organic Chemistry, 2003, vol. 68, # 3, p. 1165 - 1167
Methyl homoveratrate Preparation Products And Raw materials
Raw materialsMethanol-->(3,4-Dimethoxyphenyl)acetic acid
Preparation Products2-(3,4-Dimethoxyphenyl)ethanol-->1-(3,4-Dimethoxy-phenyl)-2-methyl-propan-2-ol
Tag:Methyl homoveratrate(15964-79-1) Related Product Information
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