4-Toluenesulfonyl chloride → p-Toluenesulphonic acid (7-methoxy-1,2,3,4-tetrahydro-naphth-2-ylmethyl) ester

Participants

Reaction Steps

20.96 g (110 mmol) of p-toluenesulphonic acid chloride are added at room temperature, while stirring, to a solution of 19.2 g (100 mmol) of 7-methoxy-1,2,3,4-tetrahydro-naphthalene-2-methanol in 80 ml of absolute pyridine, the slightly exothermic reaction being maintained at room temperature with an ice bath. The reaction mixture is stirred at room temperature for 1 hour to complete the reaction and is then diluted with ice-water and extracted with diethyl ether. The organic phase is washed while ice-cold with 2N hydrochloric acid and water, is dried over sodium sulphate, filtered and concentrated by evaporation under reduced pressure. The resulting oil is crystallised from diethyl ether/pentane to yield p-toluenesulphonic acid (7-methoxy-1,2,3,4-tetrahydro-naphth-2-ylmethyl) ester of m.p. 64°-66 °.

Provenance & Evidence