methyl 2-(2,6-dimethylphenoxy)acetate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 65 g of 2,6-dimethylphenol are dissolved in 200 ml of dry DMF and, under N2, 23.2 g of a 55% suspension of sodium hydride in mineral oil are added in portions. Then 50.4 ml of methyl bromoacetate are added dropwise with stirring, and the mixture is left to stand overnight. The precipitated salt is filtered off with suction, and the filtrate is concentrated. The residue is taken up in ethyl acetate, and the solution is extracted with water. The organic phase is dried over magnesium sulfate and concentrated. An oily liquid remains and is used directly in the following reaction. the mixture is left The precipitated salt is filtered off with suction the filtrate is concentrated the solution is extracted with water The organic phase is dried over magnesium sulfate concentrated is used directly in the following reaction

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 7 Grams of methyl 2,6-dimethylphenoxyacetate, 3.4 ml of acetic anhydride and 100 ml of carbon disulfide were mixed at 0° C., and to the mixture was added 17.9 g of aluminum chloride, and the resulting mixture was heated until gas was evolved. After the gas-evolution was ceased, the reaction mixture was refluxed for 30 minutes under heating. Then water was added to the solution. The resulting mixture was extracted with di-isopropyl ether, washed with water, dried over anhydrous magnesium sulfate. The oily solution was concentrated to obtain an oily substance. The oily substance was chromatographed on silica gel to obtain 6.1 g of methyl 4-acetyl-2,6-dimethylphenoxyacetate, nD21.6 1.5165. the resulting mixture was heated until gas the reaction mixture was refluxed for 30 minutes under heating The resulting mixture was extracted with di-isopropyl ether washed with water dried over anhydrous magnesium sulfate The oily solution was concentrated to obtain an oily substance The oily substance was chromatographed on silica gel

Conditions: temp:0.00; pressure:0.00; stir: