Formaldehyde → Chloromethyl hexanoate

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (14.27 g, 0.12 mmol) was added dropwise to hexanoic acid (11.61 g, 0.10 mmol) and the reaction mixture was heated at 70° C. for 24 hours. The reaction mixture containing hexanoyl chloride was not further purified and paraformaldehyde (3.60 g, 0.12 mol) was added and the reaction mixture heated at 120° C. until the latter disappeared (about 2 hours). The reaction mixture was distilled in vacuo and chloromethyl hexanoate was obtained as a colourless oil (b.p. 118° C., 25 mbar). 1H-NMR (CDCl3) δ 5.67 (s, 2H), 2.37-2.29 (m, 2H), 1.65-1.58 (m, 2H), 1.31-1.26 (m, 4H), 0.88 (t, 3H). 13C-NMR(CDCl3) δ 179.89, 171.77, 68.53, 33.95, 31.18, 24.34, 22.26, 13.83.

Provenance & Evidence