Potassium Carbonate → 2-[(4-Chlorobutyl)thio]benzyl alcohol

Participants

Reaction Steps

To a 5 liter 4-neck round-bottom flask fitted with mechanical stirrer, thermowell, and addition funnel, under a nitrogen atmosphere, was added 150.0 g of o-mercaptobenzyl alcohol, 2400 ml of isopropanol and 295.72 g of anhydrous potassium carbonate. The reaction mixture was cooled in an ice bath, as 246.6 ml of 1-bromo-4-chlorobutane was added dropwise. After addition was complete, the mixture was allowed to warm to room temperature, and stirred at room temperature overnight. The mixture was filtered through a pad of filter aid, and the solid was rinsed with fresh isopropanol. The solvent was removed by rotary evaporation to give 246.0 g of the product as a brown oil. 1H-NMR (CDCl3) δ 1.7-2.1(m,4H); 2.3(br s,1H); 2.85-3.0(t,2H); 3.5-3.6(t,2H); 4.75(s,2H); 7.2-7.4(m,4H).

Provenance & Evidence