Ethanol → HCID 23039690, compound

Participants

Reaction Steps

27.6 g (120 mmoles) of 2-(2,4-dichlorophenyl)-1,2-epoxypentane are dissolved in 60 ml of ethanol. A solution of 17.4 g (120 mmoles) of boron trifluoride-etherate in 60 ml of ethanol is added dropwise at 0° C., the internal temperature being kept at 0°-5° C. by cooling with ice water. The mixture is then left at +7° C. to react further slowly. As soon as epoxide can no longer be detected by gas chromatography, the reaction mixture is extracted with methylene chloride. The combined extracts are washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The yield of crude product is 32.3 g. Purification by column chromatography (silica gel; 4:1 petroleum ether/ethyl acetate) gives 15.96 g (53% of theory, taking into account that the epoxide employed is 90% pure). Boiling point 90° C./0.07mbar. 100 MHz-1H-NMR (CDCl3): δ=7.0-7.6 ppm (m, aromatic H); 3.7-4.4 ppm (m, --CH2OH); 3.2-36 ppm (q, --OCH2CH3); 1.6-2.2 ppm (m, --CH2 --, OH); 0.7-1.4 ppm (t, --OCH2CH3 and ##STR21##

Provenance & Evidence