ChemicalBook CAS DataBase List Methyl 3,4,5-trimethoxybenzoate

Methyl 3,4,5-trimethoxybenzoate synthesis

13synthesis methods

Product Name:Methyl 3,4,5-trimethoxybenzoate
CAS Number:1916-07-0
Molecular formula:C11H14O5
Molecular Weight:226.23

Methyl 3,4,5-trimethoxybenzoate can be used as a pharmaceutical intermediate and is the main raw material for the anxiolytic trimetropine, the gastrointestinal drug trimebutine maleate, etc. It can be prepared by esterification of 3,4,5-trimethoxybenzoic acid and methanol.

67-56-1 Synthesis

67-56-1
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$7.29/5ml-f

118-41-2 Synthesis

118-41-2
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$14.00/5g

1916-07-0
429 suppliers
$6.00/25g

Yield:1916-07-0 100%

Reaction Conditions:

with sulfuric acid at 65; for 24 h;

Steps:

2 4.2 Methyl 3,4,5-trimethoxybenzoate (2)
Concentrated sulfuric acid (10?mL) was added dropwise at ambient temperature to a stirring solution of compound 1 (10.0?g, 47.2?mmol) in CH₃OH (100?mL), then refluxed at 65?°C for 24?h and monitored by TLC. After completion, the reaction mixture was concentrated under reduced pressure, ethyl acetate (100?mL) was then added, and the pH was adjusted to 7.0 with saturated NaHCO₃ aqueous solution. The organic layer was separated, and the remaining water phase was extracted with ethyl acetate (80?mL) two times. The combined organic layer was washed with saturated brines and dried over anhydrous Na₂SO₄. The solvent was removed under reduced pressure to give compound 2 without further purification. Yield 100%, 10.8?g. White solid, mp 76-77?°C, literature 82-83?°C [39]. ¹H NMR (400?MHz, Chloroform-d) δ 7.23 (s, 2H), 3.84 (s, 12H).
¹³C NMR (101?MHz, Chloroform-d) δ 166.7, 152.9, 142.2, 125.1, 106.8, 60.9, 56.2, 52.2. HRMS (ESI) calcd for C₁₁H₁₄O₅ [M+Na]⁺ 249.0739, found 249.0734.

References:

Lai, Qinhuai;Wang, Yuxi;Wang, Ruixue;Lai, Weirong;Tang, Liangze;Tao, Yiran;Liu, Yu;Zhang, Ruirui;Huang, Luyi;Xiang, Haotian;Zeng, Shaoxue;Gou, Lantu;Chen, Hao;Yao, Yuqin;Yang, Jinliang [European Journal of Medicinal Chemistry,2018,vol. 156,p. 162 - 179]

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99-24-1 Synthesis