Phenol → 1-Chloro-3-phenoxy-2-propanol

Participants

Reaction Steps

A mixture of phenol (94 g; 1.0 mole) and epichlorhydrin (138.8 g; 1.5 mole) was vigorously stirred at 100° C. in the presence of piperidine hydrochloride (2.0 g) for 6 hours, cooled, and the excess epichlorohydrin removed at 100° in vacuo. The residue was cooled, dissolved in an equal volume of chloroform and stirred vigorously with excess concentrated hydrochloric acid for 0.5 hours. After separation of the phases the organic layer was washed with water, dried and evaporated to a colourless oil. Distillation gave 116.4 g (62.5%) of 1-chloro-3-phenoxy-2-propanol of bp0.6 112° as a GLC pure material, νmax (film) 3310, 1603, 1590, 1495, 1245 cm-1 ; τ(CDCl3); 7.40 (broad exchangeable s); 6.25 (2H, d, J 3.5 Hz); 5.90 (2H, s); 5.90 (1H, m); 3,21-2.56 (5H, m).

Provenance & Evidence