ethyl 3,4-dimethoxyphenylglyoxylate synthesis

7synthesis methods

Product Name:ethyl 3,4-dimethoxyphenylglyoxylate
CAS Number:40233-98-5
Molecular formula:C12H14O5
Molecular Weight:238.24

91-16-7
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4755-77-5 Synthesis

4755-77-5
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40233-98-5
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$265.82/1g

Yield:40233-98-5 99.94%

Reaction Conditions:

Stage #1: Ethyl oxalyl chloridewith aluminum (III) chloride in dichloromethane; for 0.166667 h;Inert atmosphere;Cooling with ice;
Stage #2: 1,2-dimethoxybenzene in dichloromethane at 20; for 1 h;Inert atmosphere;

Steps:

13.A A. Synthesis of ethyl-2-(3,4-dimethoxyphenyl)-2-oxo-acetate

In a round-bottom flask, in a brine and ice bath, under an argon atmosphere, aluminum chloride (1.74 g, 13.03 mmol) was suspended in dichloromethane (15 mL). To this mixture, ethyl oxalyl chloride (1.46 mL, 13.03 mmol) was added dropwise. After approximately 10 minutes, 1,2- dimethoxybenzene (1 g, 7.24 mmol) was added dropwise. After which, the reaction stirred at room temperature for one hour. Once complete, the reaction was diluted slowly with water and extracted three times with ethyl acetate. The combined organic layers are washed once with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified via silica gel column chromatography to yield ethyl-2-(3,4-dimethoxyphenyl)-2-oxo-acetate (5.17 g, 21.70 mmol, 99.94 % yield) as a colorless oil.

References:

WO2021/155367,2021,A2 Location in patent:Page/Page column 69

91-16-7
577 suppliers
$13.00/25g

40233-98-5
18 suppliers
$265.82/1g

References

89980-69-8 Synthesis