1,1-Dibromoethane → Methyl 3-octyl-tridecanoate

Participants

Reaction Steps

3 g (123.3 mmol) of magnesium was suspended in 30 ml of a dehydrated tetrahydrofuran solution under nitrogen atmosphere to activate the magnesium with dibromoethane. 120 ml of a dehydrated tetrahydrofuran solution comprising 8.0 g (22.1 mmol) of the synthesized 2-octyl-1-bromododecane was added to this solution by dropping. After dropping, the solution was stirred for two hours. The reaction mixture was cooled with ice, 2.0 ml (23.7 mmol) of dimethyl carbonate was added, and the mixture was stirred overnight at room temperature (25° C.). After filtering the reaction solution, adding diluted hydrochloric acid to the filtrate, and extracting using hexane, the solvent was evaporated under reduced pressure. The residue was distilled under the conditions of 0.15 mmHg and an oil bath temperature of 180 to 190° C. to obtain 5.0 g (14.7 mmol) of methyl 3-octyl-tridecanoate as a colorless oil. The fluidity of this compound did not decrease even when cooled to −20° C.

Provenance & Evidence