extracted with EtOAc (3 X 100 mL) and with ether (3 X 100 mL). The organic extracts were combined, washed with saturated NaCl and with water, dried over MgS04, and concentrated. The dark residue (1.3 g) was chromatographed over silica gel. The fractions eluted with CC14-CH2C12 (1:1) gave 500 mg of syrup (12.4%) which showed a strong band at 1715 cm"1 in the IR. The NMR (CDCI3) displayed signals at 8. 05-7.3 (m, 4 H), 3.85 (s, 2 H), and 2.21 ppm (s, 3 H). Crystallization from CHCl3-hexanes yielded 70 mg of 14: mp 77-78 °C; mass spectrum, m/e 216 (M+), 173, 154,133; NMR (CDClg) 8.0 (d, J = 8 Hz, 2 H), 7.5 (d, J = 8Hz, 2 H), 3.85 (s, 2 ), 2.21 (s, 3 H). The mother liquor after filtration of these crystals showed NMR and mass spectra very similar to those of the original syrup, indicating a mixture of 12 and 13. In another experiment 2.5 g of phenylacetone in 5 mL of FSO3H was stirred at room temperature for 1.75 h and added dropwise to a mixture of 75 mL of CHCI3 and ice. The aqueous phase was extracted again with 75 mL of CHC13, and the combined organic extracts were washed with saturated NaCl solution (3 x 150 mL), dried over MgS04, filtered, and concentrated to yield 1.75 g of a light brown oil. The NMR disclosed that 50% of the starting material remained. The mixture was treated again with 5 mL of FS03H at room temperature for 20 h, yielding 1.70 g of crude product in which the starting material was absent (by NMR). After two recrystallizations from CCU-CHCI3 and three from EtOH, 60 mg of 13 was obtained; mp 75.5-76 °C. Anal.
