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ChemicalBook CAS DataBase List (4-Propoxy-phenyl)-acetic acid

(4-Propoxy-phenyl)-acetic acid synthesis

5synthesis methods
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Yield:26118-57-0 40.9%

Reaction Conditions:

Stage #1: 1-(4-propoxyphenyl)ethanonewith morpholine;toluene-4-sulfonic acid;sulfur at 130; for 5 h;
Stage #2: with potassium hydroxide in ethanol;Reflux;
Stage #3: with hydrogenchloride in water; pH=2;

Steps:

78.A; 79.A

A mixture of 4-propoxy acetophenone (20 g, 0.12 mol), sulfur (17.5 g, 0.27 mol), morpholine (75 mL, 0.9 mol) and p-toluene sulfonic acid (2 g) were stirred for 5 h at 130° C. The reaction mixture was poured into 500 mL of ice water and stirred overnight. The precipitated solid was filtered and dried in vacuum to get crude compound. The crude compound and 10% potassium hydroxide in ethanol (400 mL) was refluxed overnight. Ethanol was removed in vacuum. The residue was dissolved in water and acidified (PH2) using 4N HCl. Precipitated solid was filtered, washed with water, and dried in vacuum to get crude compound. This was purified by column chromatography over silica gel (60-120 mesh) using 20% ethyl acetate in petroleum ether. Yield: 9 g (40.90%)

References:

US2011/92501,2011,A1 Location in patent:Page/Page column 112-113