Lead tetraacetate → p-Methoxyphenylpropionic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of p-methoxypropiophenone (2.39 g, 14.5 mmol), 90% lead(IV)acetate (6.45 g, 14.5 mmol), triethylorthoformate (15 ml) and 70% perchloric acid (1.2 ml. 29 mmol) was heated to 55° C. for 18 h. The mixture was cooled and the triethylorthoformate removed under reduced pressure. The residue was dissolved in CHCl3 and the remaining precipitate filtered off and discarded. The CHCl3 solution was then washed with water and evaporated to yield the crude ester. This crude ester product was dissolved in a 10% KOH 1:1 water:methanol solution, which was then refluxed for 3 h. After cooling the methanol was evaporated under reduced pressure and the aqueous solution washed with diethylether (3×25 ml). The aqueous solution was acidified with 2N H2SO4, then washed again with diethylether (3×25 ml). The combined fractions from the second ether wash were dried (Na2SO4) and evaporated to give the propionic acid (1.66 g, 63%).

Provenance & Evidence