Hydrochloric Acid → 2-Decyltetradecanoyl chloride

Participants

Reaction Conditions

Reaction Steps

A 100 mL round bottom flask is charged with 1.15 g (3.13 mmol) of 2-decyltetradecanoic acid (available as ISOCARB 24 from Sasol America), which is dissolved in 20 mL of THF with stirring under inert atmosphere. The solution is cooled to 0° C. and 1.1 mL (12.6 mmol) oxalyl chloride is added dropwise. Upon addition of N,N-dimethylformamide (DMF, 2-3 drops as catalyst), gaseous HCl is observed to evolve from the reaction mixture, after which the mixture is allowed to slowly warm to room temperature. Gas evolution ceases after 30 min, and the reaction is allowed to stir for an additional 30 min before removing solvent by rotary evaporation. The crude acid chloride is redissolved in 10 mL of fresh dry THF and then added dropwise and slowly to the appropriate amine solution, as described below.

Provenance & Evidence