ChemicalBook CAS DataBase List 3,4-Dimethoxyphenylacetone

3,4-Dimethoxyphenylacetone synthesis

7synthesis methods

Product Name:3,4-Dimethoxyphenylacetone
CAS Number:776-99-8
Molecular formula:C11H14O3
Molecular Weight:194.23

93-15-2

776-99-8

GENERAL METHOD: To a THF/water (4:1, 15 mL) solution of methyl eugenol (1 mmol) was added 10% Pd/C (0.05 mmol) and KBrO3 (3 mmol). The reaction mixture was heated to reflux temperature. The reaction progress was monitored by TLC. After completion of the reaction, the mixture was diluted with water and filtered through Whatman 40 filter paper. The filtrate was extracted with ethyl acetate and the organic layers were combined. The organic layers were washed sequentially with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography to give 3,4-dimethoxypropiophenone.

93-15-2 Synthesis

93-15-2
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776-99-8
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Yield:776-99-8 73%

Reaction Conditions:

with potassium bromate;palladium 10% on activated carbon in tetrahydrofuran;water at 65;Wacker Oxidation;

Steps:

Typical experimental procedure for Wacker oxidation with 10% Pd⁰/C-KBrO₃
General procedure: To the solution of olefine (1 mmol), in THF/water (4:1, 15 mL), 10% Pd/C (0.05 mmol) and KBrO₃ (3 mmol) were added. This mixture was heated at reflux temperature. After completion of reaction (checked by TLC), the mixture was diluted with water and filtered through Whatman 40 filter paper. The filtrate was extracted with ethyl acetate. The combined organic layer washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by column chromatography to get the product.

References:

Kulkarni, Mukund G.;Shaikh, Yunnus B.;Borhade, Ajit S.;Chavhan, Sanjay W.;Dhondge, Attrimuni P.;Gaikwad, Dnyaneshwar D.;Desai, Mayur P.;Birhade, Deekshaputra R.;Dhatrak, Nagorao R. [Tetrahedron Letters,2013,vol. 54,# 19,p. 2293 - 2295] Location in patent:supporting information

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