Benzaldehyde → 2-Phenyl-1,3-dithiane

1,3-propanedithiol (11.22 g, 103.7 mmol) was added to a solution of benzaldehyde (10.0 g, 94.2 mmol) in 150 mL of CHCl3. The mixture was stirred at room temperature for 4 h. Concentrated HCl (2 mL) was added to the reaction mixture and the resulting mixture was stirred at room temperature for additional 2 h. The mixture was washed with H2O and brine. The organic layer was dried over MgSO4 and the organic solvent was removed under reduced pressure. The crude product was purified by column chromatography (silica gel, hexanes:dichloromethane=3:1 (v/v)) to give a colorless solid (15.29 g, 83%). 1H NMR (300 MHz, CDCl3, δ): 7.43-7.48 (m, 2H), 7.25-7.36 (m, 3H), 5.15 (s, 1H), 2.85-3.10 (m, 4H), 2.10-2.20 (m, 1H), 1.84-1.99 (m, 1H). 13C{1H} NMR (75 MHz, CDCl3, δ): 138.95, 128.59, 128.29, 127.61, 51.48, 32.13, 25.15.

1. stirringthe resulting mixture was stirred at room temperature for additional 2 h
2. washThe mixture was washed with H2O and brine
3. dry with materialThe organic layer was dried over MgSO4
4. customthe organic solvent was removed under reduced pressure
5. customThe crude product was purified by column chromatography (silica gel, hexanes:dichloromethane=3:1 (v/v))

ORD record

ord-36e6399b5daf473eb9ff300453ff9a9d

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07842830B2