ChemicalBook CAS DataBase List 2-(2-Methyl-6-nitrophenyl)acetic acid

2-(2-Methyl-6-nitrophenyl)acetic acid synthesis

4synthesis methods

Product Name:2-(2-Methyl-6-nitrophenyl)acetic acid
CAS Number:23876-18-8
Molecular formula:C9H9NO4
Molecular Weight:195.17

83-41-0
8 suppliers
$13.00/25g

95-92-1 Synthesis

95-92-1
417 suppliers
$5.00/5G

23876-18-8
37 suppliers
$28.00/100mg

Yield:23876-18-8 52%

Reaction Conditions:

Stage #1: 2,3-dimethylnitrobenzene;oxalic acid diethyl esterwith potassium ethoxide in diethyl ether; for 0.25 h;Heating / reflux;
Stage #2: with sodium hydroxide;water;dihydrogen peroxide for 1.5 h;
Stage #3: with hydrogenchloride in water; pH=2;

Steps:

Diethyloxalate (3.9 g, 27 mmol) dissolved in 30 mL of diethyl ether was slowly added to a stirred mixture of 2.3 g (27 mmol) of potassium ethoxide in 6 mL of diethyl ether. When the refluxing subsided, the reaction was cooled in an ice bath and 2.8 g (18 mmol) of 3-nitro-o-xylene dissolved in 3 mL of diethyl ether was slowly added with vigorous stirring. The reaction was refluxed for 15 minutes resulting in a thick precipitate. The reaction was warmed under vacuum to remove most of the ether and 18 mL of 10% sodium hydroxide was slowly added with stirring. Hydrogen peroxide (4 mL of 30%) was slowly added accompanied by a vigorous reaction and evolution of gas. The mixture was stirred for 1.5 hours. The solids were collected by vacuum filtration, washed with water, and discarded. The filtrate and wash was combined and acidified to pH 2 with 12 N hydrochloric acid. The solids were collected by vacuum filtration, washed with water and dried under vacuum. The crude product was triturated with dichloromethane and dried under vacuum to give 1.8 g (52% yield) of 2-methyl-6-nitro-phenylacetic acid.

References:

US2004/186160,2004,A1 Location in patent:Page/Page column 22

917-58-8 Synthesis