Hydrochloric Acid → 1-Chloro-2-(2,4-dichlorophenyl)hexan-2-ol

Participants

Reaction Steps

Into a 500 ml four-necked flask equipped with a thermometer, a condenser, a mechanical stirrer, an addition funnel, and a nitrogen inlet tube are placed 102 ml (0.2 m, 1.97 M solution in hexane) of n-butyllithium. This solution is cooled to -60° with an acetone-dry ice bath. 2,4-Dichlorphenacyl chloride (44.7 g, 0.2 m) dissolved in 250 ml of ether is then added dropwise. The temperature is maintained below -55° throughout the reaction. After the addition, the reaction is allowed to warm gradually to -10° and then poured into a mixture containing 250 ml of saturated ammonium chloride and 250 ml of 10% hydrochloric acid solution. The layers are separated and the aqueous layer is extracted with 100 ml of ether. The combined ether extracts are washed with 10% hydrochloric acid, saturated sodium chloride solution, and dried over MgSO4. Solvent is evaporated to give 52 g of a pale yellow oil. Vacuum distillation (100°-120°/0.2 mm) affords 44 g of pure product.

Provenance & Evidence