Hydrochloric Acid → 2-ethyl-2-(hydroxymethyl)hexanoic Acid

Participants

Reaction Conditions

Reaction Steps

27 ml (72.9 mmol) of n butyllithium (2.7 M in heptane) are added dropwise at 0° C. to a solution of 10.9 ml of diisopropylamine (77.5 mmol) in 60 ml of THF, and the mixture is stirred at 0° C. for 30 min. Within 10 min, 5 g (34.7 mmol) of 2-ethylhexanoic acid are added dropwise at 0° C. and the reaction mixture is heated to 50° C. for 1.5 h. The clear solution is cooled to 0° C. and admixed with 3.1 g (103 mmol) of paraformaldehyde. After 10 min at 0° C., the mixture is stirred at RT for 18 h. The mixture is admixed with saturated aqueous solution of ammonium chloride and adjusted to pH=1-2 with 6N of HCl. The organic phase is removed, the aqueous phase is re-extracted once with MTBE and the combined organic phases are concentrated on a rotary evaporator. The yield of pure product is 89% (GC).

Provenance & Evidence