Benzaldehyde → 2-Phenyl-1,3-dithiane

To a solution of benzaldehyde (10.6 g, 100 mmol) and 1,3-propane dithiol in CH2Cl2 (150 mL) at room temperature was dropwise added BF3.Et2O (6.3 mL, 50 mmol) and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was then diluted with CH2Cl2, filtered and the filtrate washed with brine, saturated NaHCO3, brine and dried over Na2SO4. The solvent was removed under reduced pressure to afford a white solid, which was recrystallized from a 1:1 mixture of ether and hexane to afford 17.0 g (87%) of the title compound (21) as white crystalline needles. 1H NMR (CDCl3, 400 MHz): δ 1.91 (m, 1H), 2.14 (m, 1H), 2.89 (m, 2H), 3.04 (m, 2H), 5.16 (s, 1H), 7.35-7.28 (m, 3H), 7.46 (m, 2H).

1. customat room temperature
2. filtrationfiltered
3. washthe filtrate washed with brine, saturated NaHCO3, brine
4. dry with materialdried over Na2SO4
5. customThe solvent was removed under reduced pressure
6. customto afford a white solid, which
7. customwas recrystallized from a 1:1 mixture of ether and hexane

ORD-Eintrag

ord-13a3816c384b4f36bc059bced32ce075

Quelldatensatz

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07560483B2