1-methyl-4-[(4-methylphenyl)methylsulfanylmethyl]benzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 85.1 g (0.351 mol) of di-(p-methylbenzyl) sulfide and 51.5 g (0.421 mol) of p-methylbenzyl alcohol are initially introduced into 250 ml of methylene chloride under an N2 atmosphere in a reaction vessel (750 ml) provided with a stirrer and thermometer. 142.7 g of an approximately 54% by weight HBF4 solution in diethyl ether is added dropwise at an internal temperature of 20°-30° C. in the course of 40 min, while stirring. The reaction mixture is stirred at RT for 2 h. The reaction mixture is diluted with methylene chloride and extracted 4 times by shaking with deionized water (pH 5-6). The organic phase is dried with MgSO4 and the methylene chloride is removed on a rotary evaporator. The product, which has not been completely freed from methylene chloride, is stirred in 250 ml of toluene at RT for about 1 h and then at 0°-5° C. for 1 h. The crystals which have now precipitated are filtered off with suction and washed with a little toluene. The product is dried under a high vacuum at room temperature for 19 h. 118.6 g of tris-(p-methylbenzyl)-sulfonium tetrafluoroborate are obtained as white crystals of melting point 168°-170° C. provided with a stirrer The reaction mixture is stirred at RT for 2 h extracted 4 times by shaking with deionized water (pH 5-6) The organic phase is dried with MgSO4 the methylene chloride is removed on a rotary evaporator is stirred in 250 ml of toluene at RT for about 1 h The crystals which have now precipitated are filtered off with suction washed with a little toluene The product is dried under a high vacuum at room temperature for 19 h

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 269.0 g (1.12 mol) of sodium sulfide hydrate and 12.0 g of tetrabutylammonium hydrogen sulfate (phase transfer catalyst) in 300 ml of water is introduced into a reaction vessel provided with a stirrer and thermometer. 212.6 g (1.52 mol) of 4-methylbenzyl chloride are added dropwise at below 40° C. in the course of 30 minutes (min), while stirring intensively. The reaction mixture is stirred at room temperature (RT) for 4 1/2 hours (h) and then at 50°-60° C. for 1/2 h. The reaction mixture is cooled to 0°-5° C. and kept at this temperature for 1/2 h. The reaction mixture is filtered and the residue is dissolved in about 2 liters of ethyl acetate. The organic phase is extracted twice by shaking with deionized water (pH ~6) and dried over MgSO4. The ethyl acetate is removed on a rotary evaporator. The residue is dried overnight at RT under a high vacuum. 174.8 g (95% of theory) of di-(p-methylbenzyl) sulfide are obtained as slightly yellowish white crystals having a melting point of 74°-76° C. provided with a stirrer The reaction mixture is stirred at room temperature (RT) for 4 1/2 hours (h) The reaction mixture is cooled to 0°-5° C. kept at this temperature for 1/2 h The reaction mixture is filtered the residue is dissolved in about 2 liters of ethyl acetate The organic phase is extracted twice by shaking with deionized water (pH ~6) dried over MgSO4 The ethyl acetate is removed on a rotary evaporator The residue is dried overnight at RT under a high vacuum