Benzaldehyde → 2-Phenyl-1,3-dithiane

Benzaldehyde (11.5 mL, 112 mmol and 1,3-propanedithiol (120 mL, 92.5 mmol) were stirred in methylene chloride (200 mL) at 0° C. and HCl(g) was bubbled into the solution followed by addition of zinc chloride (9 g). The mixture was stirred overnight after which it was poured onto 10% potassium hydroxide solution. The layers were separated and the organic extract was washed with 10% potassium hydroxide solution, water, brine and dried (MgSO4). Evaporation of solvent at reduced pressure afforded an oil which crystallized upon standing and was recrystallized from diethyl ehter to give 16.2 g (89%) of product. 1H NMR (CDCl3) δ: (m, 2H), 5.16 (s, 1H), 7.25-7.36 (m, 3H), 7.45-7.48 (m, 2H) ppm.

1. customHCl(g) was bubbled into the solution
2. additionfollowed by addition of zinc chloride (9 g)
3. additionwas poured onto 10% potassium hydroxide solution
4. customThe layers were separated
5. extractionthe organic extract
6. washwas washed with 10% potassium hydroxide solution, water, brine
7. dry with materialdried (MgSO4)
8. customEvaporation of solvent at reduced pressure
9. customafforded an oil which
10. customcrystallized
11. customwas recrystallized from diethyl ehter

ORD record

ord-358e6159115a4b7989803e6228192daa

Source dataset

uspto-grants-1989_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04877779