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3,4-DIMETHOXYBENZHYDROL synthesis

5synthesis methods
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Yield:56139-08-3 80%

Reaction Conditions:

Stage #1: bromobenzenewith iodine;magnesium in diethyl ether at 0; for 0.166667 h;
Stage #2: 3,4-dimethoxy-benzaldehyde in diethyl ether; for 12 h;

Steps:

General procedure for the preparation of 1a, 1b, 1c, 1g and 1h:

General procedure: A 50 mL round-bottom flask was charged with bromobenzene (157 mg, 1 mmol), anhydrous Et2O (10 mL), magnesium powder (24 mg, 1 mmol) and a little iodine added. The mixture was cooled to 0 °C and stirred for 10 min, then a solution of 3-methoxybenzaldehyde (136 mg, 1 mmol) and anhydrous Et2O was added slowly. The solution was stirred for 12 h after the temperature rose to room temperature; 5 mL NH4Cl aqueous solution was dropped slowly, and the mixture extracted with Et2O (3×30 mL). The combined organic layers were dried with anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was isolated by flash column chromatography on silica gel to give the products.

References:

Zhang, Wei;Zhang, Wenxue;Dai, Yisi;Zhu, Haizhen [Tetrahedron Letters,2013,vol. 54,# 13,p. 1747 - 1750] Location in patent:supporting information