2,4-Dichlorobenzyl chloride → 2,4-Dichlorobenzyl alcohol

Participants

Reaction Steps

Aqueous sodium hydroxide (40 ml of 70% w/v solution) was added slowly with stirring to glacial acetic acid (42 g). The temperature rose to reflux and tetrabutylammonium hydrogen sulphate (0.5 g) and 2,4-dichlorobenzyl chloride (100 g) were added and the mixture heated under reflux for eight hours. The mixture was cooled to 70°-75° C. and aqueous sodium hydroxide (35 ml of 70% w/v solution) added. The temperature was maintained in the range 70°-75° C. for 30 minutes. The product was extracted into petroleum ether (boiling range 80°-100° C. 90 ml) at 75° C. and the organic extract was diluted with petroleum ether (150 ml), washed with dilute aqueous hydrochloric acid, and filtered. The filter was washed with petroleum ether (40 ml) and the filtrate and washings combined and allowed to cool to give crystals of 2,4-dichlorobenzyl alcohol having a purity of 99.8% and in a yield of 95%.

Provenance & Evidence