Methyl syringate synthesis
- Product Name:Methyl syringate
- CAS Number:884-35-5
- Molecular formula:C10H12O5
- Molecular Weight:212.2
1916-07-0
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Yield:884-35-5 98%
Reaction Conditions:
Stage #1:3,4,5-trimethoxybenzoic acid methyl ester with aluminum (III) chloride in dichloromethane at 20;
Stage #2: with hydrogenchloride;water in dichloromethane;chloroform
Steps:
1.1 STEP 1: Preparation of methyl 3,5-dimethoxy-4-hydroxybenzoate
Aluminum chloride (III) (7.22 g, 54.1 mmol) was slowly added to methyl 3,4,5-trimethoxybenzoate represented by Formula 86 (3.50 g, 15.5 mmol, purchased from Sigma-Aldrich Co.) in dichloromethane (200 mL) at room temperature.
After agitating the reaction mixture at room temperature, the solution was diluted with chloroform, washed with a 2N hydrochloric acid solution, followed by separation to form an organic layer.
The organic layer was dried with sodium sulfate and the solvent was removed under reduced pressure.
The remaining vacuum-concentrated mixture was subjected to separation and purification through column chromatography (chloroform/methanol, 20:1, v/v) using silica gel (SiO2), resulting in a phenol compound represented by Formula 87 as a desired product (3.20 g, 98%).
Analysis data of the above product is provided as follows.
Rf (ethyl acetate <55>/hexane, 1:1) 0.4;
1H NMR (500 MHz, DMSO-d6) d 3.81 (s, 9 H), 7.22 (s, 2 H).
References:
Vivozon Inc.;LEE, Doo Hyun EP2786986, 2014, A2 Location in patent:Paragraph 0063-0064
27065-65-2
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