1,3-Propanedithiol → HCID 19843048, compound

Hex-5-ynal (20 g, 0.2M) and 1,3-propanedithiol (20 mL, 0.2 mmol) were stirred in 300 mL methylene chloride at 0°-5° C. and HCl(g) was bubbled into the solution for 10 minutes when it became cloudy. The mixture was stirred 2 days after which it was poured onto 100 mL of 10% KOH. The organics were washed again with 10% KOH (25 mL), then brine, and dried (MgSO4) before evaporation at reduced pressure. The residue was Kugelrohr distilled at 0.1 mm, oven 110° C. to give 27 g of product (72%). 1H NMR (CDCl3) δ 1.7-1.8 (m, 2H), 1.8-1.95 (m, 3H), 1.99 (t, J=2.6 Hz, 1H), 2.2-2.25 (m, 2H), 2.8-2.95 (m, 4H), 4.06 (t, J=6.9 Hz, 1H).

1. customHCl(g) was bubbled into the solution for 10 minutes when it
2. additionwas poured onto 100 mL of 10% KOH
3. washThe organics were washed again with 10% KOH (25 mL)
4. dry with materialbrine, and dried (MgSO4)
5. custombefore evaporation at reduced pressure
6. distillationdistilled at 0.1 mm, oven 110° C.

ORD record

ord-a1629e085eaf4b76a988e08ae61dc01b

Source dataset

uspto-grants-1989_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04877779