Pyridine → Chloromethyl 1-methylcyclohexyl carbonate

Participants

Reaction Steps

1-Methylcyclohexanol (4.57 g) in dichloromethane (40 ml) was cooled in an ice-bath and treated with pyridine (3.24 ml). Chloromethyl chloroformate (3.65 ml) in dichloromethane (10 ml) was added dropwise through a pressure-equalising funnel. The mixture was stirred for 2 h and then washed with water (2×), dried (MgSO4) and then evaporated to leave a reddish-coloured oil, which was dissolved in dichloromethane and filtered through silica gel (230-400 mesh ASTM) to give (after evaporation) chloromethyl 1-methylcyclohexyl carbonate as a colourless oil (8.97 g), υmax(CH2Cl2) 2940, 2865, 1763, 1444, 1346, 1292, and 1237 cm−1; δ(CDCl3) 1.25-1.70 (11H, m), 2.12-2.18 (2H, m), 5.69 (2H,s) ppm.

Provenance & Evidence