Toluene → Methyl 16-bromohexadecanoate

Participants

Reaction Conditions

Reaction Steps

16-Bromohexadecanoic acid (6 g, 17.9 mmol) was dissolved in methanol (35 mL), toluene (100 mL) and trimethylorthoformate (20 mL). Amberlyst 15 was added and the mixture was stirred under nitrogen for 16 h at 55° C. The mixture was concentrated, and dissolved in methanol (ca. 50 mL) and DCM (30 mL). The resin was filtered off, and the filtrate was concentrated. The volume was increased to ca. 40 mL with methanol. Cooling produced crystals which were filtered off, washed with cold methanol and dried to yield white crystals (5.61 g, 90% yield).

Provenance & Evidence