Sodium Sulfite → 6-Cyanohexane-l-sulfinic acid sodium salt

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[N:9].[S:10]([O-])([O-:12])=[O:11].[Na+:14].[Na+]>CCO.O>[Na+:14].[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][S:10]([O-:12])=[O:11])#[N:9]

Participants

Procedure

##STR13## In a three necked flask, fitted with a water condenser, a mechanical stirrer and a dropping funnel a solution of 1-bromo-6-cyanohexane (8.04 g, 42.3 mmol) was placed in 75 mL of 95% EtOH. The mixture was heated to reflux and to it was slowly added a solution of sodium sulfite (8.00 g, 63.5 mmol) in 50 mL of H2O over a period of 30 min. The mixture was heated for 2 h and then concentrated under reduced pressure. The residue was dissolved in 95% EtOH (200 ml), heated to boiling and filtered. The filtrate was concentrated and cooled in an ice bath. The precipitate was collected by filtration and dried to give 3.00 g of a white solid. The mother liquor on further concentration, produced another batch of 2.2 g of the product. 1H NMR (300 MHz, DMSO-d6) δ 2.50 (t, j=8 Hz, 2H), 2.40(t, 8 Hz, 2H), 1.55 (m, 4H), 1.3(m, 4H).