Sulfuric Acid → 4-Oxo capric acid

Participants

Reaction Steps

Triethylamine (10.1 g, 0.1 mol) is added to a solution of heptanal (11.4 g, 0.1 mol), acrylonitrile (5.31 g, 0.1 mol) and 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride (2.69 g, 0.01 mol) and the mixture stirred for 8 hours. The mixture is poured into 1% H2SO4 (150 ml) and extracted with CHCl3 (4×50 ml). This extract is washed with water, NaCO3 solution, and dried over NaSO4 to yield a brown oil. After distillation, (bp 150-175/0.08 mbar), the colourless oil obtained (9.5 g) is hydrolysed with 2.5M NaOH (100 ml) to yield 4.5 g of 4-oxodecanoic acid as a pale brown semi-solid.

Provenance & Evidence