Preparation and etherification reaction of fatty dichlorocyclopropanes

Dichlorocarbene was added tocis-9-octadecene, methyl oleate, methyl elaidate, and methyl linoleate to form the corresponding mono- or bis-dichlorocyclopropanes in yields of 75–88%. The dichlorocyclopropanes underwent ring-opening substitution on heating with alcohols (or water) to form β-chlorallylic ethers (or alcohols). The ethers were obtained in yields of 46 to 84%. Tetraethylene glycol and methyl lactate, as hydroxyl compounds, gave a polyethenoxy ester and an ether-linked diester, respectively. Presented at AOCS meeting, Toronto, October, 1962. F. Utiliz. Res. & Dev. Div. ARS, U.S.D.A.