ChemicalBook CAS DataBase List 2,6-Dimethoxybenzoic acid

2,6-Dimethoxybenzoic acid synthesis

12synthesis methods

Product Name:2,6-Dimethoxybenzoic acid
CAS Number:1466-76-8
Molecular formula:C9H10O4
Molecular Weight:182.17

2,6-Dimethoxybenzoic acid is the key intermediate in the preparation of gamma-resorcylic acid which has been described as having activity against rheumatic fever.
The Preparation of 2,6-Dimethoxybenzoic Acid
Cite this: J. Org. Chem. 1956, 21, 3, 368–369
Publication Date:March 1, 1956
https://doi.org/10.1021/jo01109a604

124-38-9
131 suppliers
$214.00/14L

151-10-0
460 suppliers
$5.00/10g

1466-76-8
275 suppliers
$5.00/25mg

Yield:1466-76-8 71%

Reaction Conditions:

Stage #1: 1,3-Dimethoxybenzenewith sodium
Stage #2: carbon dioxide

Steps:

1 EXAMPLE 1 Preparation of 2,6-Dimethoxybenzoic Acid

5.90 g (0.256 M) of sodium and 200 ml of anhydrous toluene are introduced into a reactor. The mixture is refluxed for 30 min and then stirred vigorously at room temperature. 12.6 g (0.09 M) of 1,3-dimethoxybenzene and 17.7 g (0.119 M) of chlorooctane are then added successively. After stirring for 2 h at room temperature, about 35 g of CO2 are added and the reaction is stirred for 12 h at room temperature. The excess sodium is then neutralized with 10 ml of methanol. After acidification using concentrated hydrochloric acid solution, the medium is concentrated under partial pressure. The residue is dissolved in acetone. The inorganic salts are removed by filtration. Recrystallization is carried out in an acetone/hexane mixture. 11.3 g of 2,6-dimethoxybenzoic acid (yield=68%) are thus obtained. Characteristics of the product obtained: 1H NMR DMSO-d6) =3.89 ppm (s, 6H), 6.60 ppm (d, 2 H), 7.34 (t, 1H), 8-9 (s,1H). By replacing the chlorooctane with chloropropane, 2,6-dimethoxybenzoic acid is obtained in a yield of 71%.

References:

US6384273,2002,B1 Location in patent:Page column 7-8

201230-82-2 Synthesis