Water → But-3-enyl 4-methylbenzenesulfonate

Participants

Reaction Conditions

Reaction Steps

29.3 millimoles of 3-buten-1-ol are added to a solution of 525 millimoles of p-toluenesulphonyl chloride in 200 ml of anhydrous pyridine cooled to 0° C. The mixture thus obtained is kept stirred overnight at −5° C. It is then added with stirring to a mixture of 200 g of water and ice. An oily product is extracted from the aqueous mixture by 3 ether washes, each of 300 ml. The ether fractions are washed twice with 300 ml of a cold solution of hydrochloric acid (HCl:water being 1:1 by weight) to remove pyridine, and then with 300 ml of water, and are then dried over potassium carbonate and sodium sulphate and decolorized with active carbon. The suspension is filtered and the ether is evaporated from the filtrate at reduced pressure to leave an oily product. The oily product is then washed with cold pentane to remove the impurities and obtain γ-butenyl 1-tosylate.

Provenance & Evidence