1,3-Propanedithiol → HCID 19843048, compound

Participants

Reaction Steps

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).

Provenance & Evidence