Sodium Hydroxide → 1-Indanone

Participants

Reaction Steps

Racemic 2-phenylindanone VI is the starting material for the process of the invention. As shown in Step B, indanone VI is directly converted to the methylated intermediate VII containing the (+) and (-) enantiomers by treating indanone VI with methyl halide and an aqueous base (e.g., 50% aqueous sodium hydroxide) in an organic solvent (e.g., toluene) in the presence of a chiral catalyst at a temperature, of about 15° C. The 2-methylated (+) and (-) enantiomer of intermediate VII can then be O-demethylated in the presence of a catalyst (AlCl3) to obtain the optically active intermediate (+) and (-) enantiomer indanone mixture VIII which, in turn, can then be alkylated, hydrolyzed, and acidified to obtain the pure (+) and (-) enantiomers of indenyl-oxy acetic acid I at a yield of about 65-80%.

Provenance & Evidence