Sodium Iodide → Iodomethyl pivalate

Participants

Reaction Steps

Sodium iodide (dried) (15.0 g, 100 mmol) was added in one portion to a solution of 2,2-dimethylpropanoic acid, chloromethyl ester (10.0 g, 66.7 mmol) in dry acetonitrile (80 mL) at RT under argon. The heterogeneous reaction was stirred at RT for 6 h, then concentrated in vacuo. The residue was partitioned between toluene (150 mL) and 5% sodium bisulfite (40 mL). The organic layer was washed with 5% sodium bisulfite (40 mL) and water (20 mL), then dried over MgSO4. Evaporation gave title iodide (12.1 g, 75%) as a pale yellow oil.

Provenance & Evidence