1-Butanol → HCID 23039675, compound

Participants

Reaction Steps

A solution of 4.56 g (30 mmoles) of 2-(4-fluorophenyl)-1,2-epoxypropane in 5.55 g (75 mmoles) of n-butanol is added dropwise slowly at an internal temperature of 5°-7° C., with cooling, to a solution of 2.13 g (0.016 mole) of boron trifluoride ethyl etherate in 5.55 g (75 mmoles) of n-butanol, and the temperature is kept at +7° C. for a further 4 hours. The reaction mixture is then worked up by extraction (methylene chloride) and washing with water. The organic phase is dried over sodium sulfate, filtered and concentrated in vacuo. Distillation of the crude product gives 4.48 g (=66% of theory) of the pure end product in the form of a colourless oil. Boiling point 120°-125° C./20 mbar. 100 MHz-1H-NMR (CDCl3): δ=6.8-7.5 ppm (m, 4H aromatic); 3.5 ppm (q, 2H, --CH2OH); 3.2 ppm (m, 2H, --OCH2 --); 2.3 ppm (broad, 1H, --OH); 1.6 ppm (s, 3H, --CH3); 1.4 ppm (m, 4H, --CH2CH2 --); 0.9 ppm (t, 3H, --CH3).

Provenance & Evidence