Sodium Iodide → HCID 22145405, compound

Participants

Reaction Steps

Chloromethyl 1-methylcyclohexyl carbonate (2.07 g) in acetone (7.5 ml) was treated with 2,6-lutidine (0.116 ml). Sodium iodide (2.25 g) was then added and the mixture was stirred for 1.5 h. More sodium iodide (1.5 g) was then added and stirring was continued. After a total of 2.5 h the acetone was removed and CH2Cl2/water were added and the layers separated. The dichloromethane layer was washed with 5% aqueous Na2S2O3, dried (MgSO4) and evaporated to leave an oil. This was taken up in hexane (50 ml) and loaded onto a silica gel column, and the column was eluted with 5% ethyl acetate in hexane to give iodomethyl 1-methylcyclohexyl carbonate containing some of the starting chloromethyl compound, δ(CDCl3) 1.26-1.35 (2H, m), 1.40-1.65 (9H, m, including s at δ 1.52), 2.10-2.20 (2H, m), 5.69 (s) and 5.91 (s) (together 2H, ratio 1:5) ppm.

Provenance & Evidence