Butanal → 2-Ethyl-4-methyl-1,3-oxathiane

A solution of 3-mercapto-1-butanol (106 g, 1 mol, synthesized as above) and PTSA (paratoluenesulfonic acid monohydrate, 38 g, 0.2 mol, commercially available from Sigma-Aldrich, Inc.) in 400 mL of CH2Cl2 (dichloromethane) were cooled with an ice bath. Butyraldehyde (106 mL, 1,2 mol, commercially available from Sigma-Aldrich, Inc.) was added drop wise to the solution, and the reaction mixture was stirred with cooling for half an hour and at room temperature for another 1 hour. The reaction mixture was washed twice with saturated sodium bicarbonate solution and once with brine. The organic phase was then dried with anhydrous magnesium sulfate. The solvent was removed with a rotary evaporator and the crude product was distilled under vacuum to provide 2-ethyl-4-methyl-1,3-oxathiane (98 g), which had a boiling point of 80° C. at a pressure of 10.4 mmHg.

1. addition) was added drop wise to the solution
2. washThe reaction mixture was washed twice with saturated sodium bicarbonate solution and once with brine
3. dry with materialThe organic phase was then dried with anhydrous magnesium sulfate
4. customThe solvent was removed with a rotary evaporator
5. distillationthe crude product was distilled under vacuum

ORD record

ord-1b0f5433964b4bfd924d03e1abb8d17d

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173822B2