[CH2:1]([C:3]1[CH:15]=[CH:14][C:6]([C:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=O)=[CH:5][CH:4]=1)[CH3:2].C1(C)C=CC=CC=1>O.Cl.[Zn]>[CH2:1]([C:3]1[CH:15]=[CH:14][C:6]([CH2:7][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1)[CH3:2]To a 500 mL round-bottomed flask equipped with condenser and nitrogen inlet were added 41.2 grams (200 mmol) 3-(4-ethylbenzoyl)-propionic acid, activated zinc prepared from 82.4 grams (400 mmol) mossy zinc and 8.2 grams mercuric chloride in 125 mL water and 8 mL concentrated hydrochloric acid, 77 mL water, 177 mL concentrated hydrochloric acid, and 100 mL toluene. The mixture was refluxed 60 hours with addition of two 50 mL portions of concentrated hydrochloric acid, cooled, and the layers separated. The organic layer was extracted into 3N aqueous sodium hydroxide, which was then acidified and extracted into ethyl acetate. The organic layer was dried over sodium sulfate and evaporated to afford 28.9 grams (75%), M.P. 70°-72° C.
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