ChemicalBook CAS DataBase List 2,6-Dimethoxybenzaldehyde

2,6-Dimethoxybenzaldehyde synthesis

5synthesis methods

Product Name:2,6-Dimethoxybenzaldehyde
CAS Number:3392-97-0
Molecular formula:C9H10O3
Molecular Weight:166.17

151-10-0
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109-94-4 Synthesis

109-94-4
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3392-97-0
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$10.00/1g

Yield:3392-97-0 48%

Reaction Conditions:

Stage #1:1,3-Dimethoxybenzene with n-butyllithium in tetrahydrofuran;hexane at 0; for 2 h;
Stage #2:formic acid ethyl ester in tetrahydrofuran;hexane at -78; for 3 h;
Stage #3: with ethanol;iodine;potassium carbonate in tetrahydrofuran;hexane at -78 - 20; for 15 h;

Steps:

4.2. Typical procedure for one-pot conversion of aromatic bromides into aromatic ethyl esters with ethyl formate
General procedure: n-BuLi (1.67 M solution in hexane, 1.32 mL, 2.2 mmol) was added dropwise into a solution of p-bromochlorobenzene (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, ethyl formate (1.6 mL, 20 mmol) was added to the mixture and the obtained mixture was stirred at -78 °C. After 3 h at the same temperature, I₂ (1523 mg, 6 mmol), K₂CO₃ (1382 mg, 10 mmol) and EtOH (3 mL) were added at -78 °C and the mixture was stirred for 14 h at rt. The reaction mixture was quenched with satd aq Na₂SO₃ (5 mL) and was extracted with CHCl₃ (3×20 mL). The organic layer was washed with brine and dried over Na₂SO₄ to provide ethyl 4-chlorobenzoate in 77% yield. If necessary, the product was purified by short column chromatography (SiO₂:hexane:EtOAc=9:1) to give pure ethyl 4-chloro-1-benzoate as a colorless oil.

References:

Ushijima, Sousuke;Moriyama, Katsuhiko;Togo, Hideo [Tetrahedron,2012,vol. 68,# 24,p. 4701 - 4709] Location in patent:experimental part

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4885-02-3 Synthesis