Hydrochloric Acid → [4-(Chloromethyl)phenyl]methanol

Participants

Reaction Conditions

Reaction Steps

1,4-benzenedimethanol (13.8 g, 0.10 mole) was dispersed in chloroform (100 mL) in a 500 mL three-neck round bottom flask equipped with a magnetic stirring bar, an addition funnel, a nitrogen inlet and a gas scrubber. The mixture was cooled to 0° C. in an ice bath. Thionyl chloride (13.1 g, 0.11 mole) dissolved in chloroform (10 mL) was added dropwise over ten minutes with rapid stirring to the cooled mixture. As the addition proceeded, the mixture largely cleared. During the addition step, and for one hour thereafter, the reaction flask was swept with nitrogen which was then passed through the scrubber before venting to the atmosphere. The nitrogen was turned off and the scrubber disconnected. The mixture was allowed to come to room temperature and stirring was continued for 20 hours. Sufficient sodium bicarbonate was added to neutralize any residual hydrogen chloride. The mixture was filtered through a coarse glass frit and the solvent removed under reduced pressure at 35° C. A sample of the residue was chromatographed on silica gel (200 g) with an ethyl acetate:hexane (2:3) solvent. p-Hydroxymethyl-benzyl chloride was obtained in 75% yield (11.64 g). The product had a melting point of 58°-60° C. NMR spectral data were as follows: 1H NMR (CDCl3, 300 MHz): δ7.3 (m, 4H), 4.70 (s, 2H), 4.59 (s, 2H), 1.67 (s, 1H); 13C NMR (CDCl3, 75 MHz, ppm) 141.372, 135.995, 128.876, 127.366, 64.927, 46.121.

Provenance & Evidence