Epichlorohydrin → 1,5-Dithiocan-3-ol

A first solution of 1,3-propanedithiol (10.82 grams, 0.10 moles, commercially available from Alfa Aesar; Ward Hill, Mass.) and ethanol (45 milliliters) was placed in a 60-milliliter syringe. A second solution of epichlorohydrin (9.25 grams, 0.10 moles) and ethanol (45 milliliters) was placed in a second 60-milliliter syringe. Both solutions were slowly added dropwise to a mixture of sodium hydroxide (8.80 grams, 0.22 moles) and ethanol (250 milliliters) at room temperature over 10 hours. After stirring for an additional 8 hours, the reaction mixture was concentrated under vacuum, and then diluted with ethyl acetate (200 milliliters). The organic phase was washed with water (200 milliliters) and saturated sodium chloride in water (100 milliliters) and dried over magnesium sulfate. The solvent was removed under reduced pressure to give the crude product that was purified by column chromatography over silica gel using a mixture of ethyl acetate in hexane (30/70 parts by weight). The product was isolated as an oil. (6.99 grams, 43% yield).

1. concentrationthe reaction mixture was concentrated under vacuum
2. additiondiluted with ethyl acetate (200 milliliters)
3. washThe organic phase was washed with water (200 milliliters) and saturated sodium chloride in water (100 milliliters)
4. dry with materialdried over magnesium sulfate
5. customThe solvent was removed under reduced pressure

ORD record

ord-42af5c370fad46b9b51f4a6f33820df8

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07495054B2