반응 #6482

반응 방정식

potassium hydroxide

phenylacetaldehyde

1,3-propanedithiol

boron trifluoride etherate

→

title compound

수율 91.0%

2-Phenylmethyl-1,3-dithiane

수율 91.0%

용매

methylene chloride

반응 조건

후처리

1. 1
   기타The layers were separated
2. 2
   추출the aqueous layer was extracted with methylene chloride
3. 3
   추출The combined organic extract
4. 4
   세척was washed with 1N aqueous sodium hydroxide solution and brine
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   여과filtered
7. 7
   workup.DISTILLATIONthe filtrate was distilled

실험 절차

To a solution of 33.9 g (280 mmol) of phenylacetaldehyde and 35.6 g (330 mmol) of 1,3-propanedithiol in 300 mL of methylene chloride at 0° C., was added, dropwise over a period of 30 minutes, 10 mL of boron trifluoride etherate. The reaction mixture was allowed to warm to ambient temperature and stirred for 3 h at ambient temperature. The reaction mixture was made basic by the addition of 180 mL of 5% aqueous potassium hydroxide solution and the resultant mixture was stirred for 0.5 h. The layers were separated and the aqueous layer was extracted with methylene chloride. The combined organic extract was washed with 1N aqueous sodium hydroxide solution and brine, dried over anhydrous magnesium sulfate, filtered and the filtrate was distilled to afford 53.62 g (91% yield) of the title compound, b.p. 150° C. (2 mm Hg); 1H NMR (CDCl3) δ1.75-1.95 (1H, m), 2.05-2.17 (1H, m), 2.75-2.91 (4H, m), 3.03 (2H, d, J=9 Hz), 4.25 (1H, t, J=9 Hz), 7.17-7.38 (5H, m).

출처