Reaktion #6482

Reaktionsgleichung

potassium hydroxide

phenylacetaldehyde

1,3-propanedithiol

boron trifluoride etherate

→

title compound

Ausbeute 91.0%

2-Phenylmethyl-1,3-dithiane

Ausbeute 91.0%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe layers were separated
2. 2
   Extraktionthe aqueous layer was extracted with methylene chloride
3. 3
   ExtraktionThe combined organic extract
4. 4
   Waschenwas washed with 1N aqueous sodium hydroxide solution and brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   workup.DISTILLATIONthe filtrate was distilled

Vorschrift

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).

Quelle