3-PHENYL-4'-THIOMETHYLPROPIOPHENONE synthesis

6synthesis methods

Product Name:3-PHENYL-4'-THIOMETHYLPROPIOPHENONE
CAS Number:40027-88-1
Molecular formula:C16H16OS
Molecular Weight:256.36

21382-98-9
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$67.40/25g

90878-19-6
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$87.50/100ml

40027-88-1
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$433.00/1g

Yield:40027-88-1 96%

Reaction Conditions:

with hydrogenchloride in tetrahydrofuran;

Steps:

19.a 19a.

19a. 1-(4-Methylthiophenyl)-3-phenylpropan-1-one To a stirred solution of 4-(methylthio)benzonitrile (25.0 g, 0.17 mol) in THF (100 mL) under N₂ atmosphere was added phenethylmagnesium chloride (1.0 M in THF, 210 mL, 0.21 mol). The solution was heated to reflux for 4 hours, cooled to 0 OC, and quenched carefully with water (10 mL). The resulting slurry was treated with 6 N hydrochloric acid (200 mL) and stirred at room temperature overnight. The THF was evaporated from the mixture, and the residue was extracted with EtOAc (2 X 300 mL). The combined organic extracts were washed with 2M NACO, dried over Na₂SO₄, filtered, and concentrated to give a solid material. Recrystallization from EtOAc-Hex (1:4) afforded the title compound (41.5 g, 96%) as greenish plates. mp 105 ^-C. ¹H NMR (300 MHz, CDCl₃) δ7.85 (d, J=8.5 Hz, 2H), 7.32-7.19 (m, 7H), 3.24 (t, J=6.8 Hz, 2H), 3.06 (t, J=6.8 Hz, 2H), 2.50 (s, 3H); ¹³C NMR (75 MHz, CDCl₃) 8 198.2, 145.8, 141.3, 133.2, 128.48, 128.42, 128.38, 126.1, 125.0,40.2,30.2, 14.7; mass spectrum (API-TIS) m/z 257 (M+H).

References:

US2001/41726,2001,A1

100-42-5 Synthesis