Methyl iodide → Benzene, 1,2,4,5-tetrakis(methylthio)-

Participants

Reaction Conditions

Reaction Steps

Into a 3-neck 1 liter flask equipped with a thermometer, magnetic stirring bar, and gas inlet and outlet tubes was placed a solution of 25 g (66.72 millimoles) of the product of Example 1 in 300 ml of dry pyridine. The mixture was heated rapidly to 105°-110° C. and 8.29 g of Na pellets (360 millimoles) were added rapidly against a nitrogen flow. The reaction mixture was maintained below reflux but above 100° C. for 1 hour until all of the sodium had reacted. The mixture was then cooled to 10° C. and methyl iodide (24 ml) was added slowly by means of a syringe. The resulting mixture was stirred for 40 minutes and quenched with 350 ml of saturated aqueous NaCl. Water was then added to form a dilute suspension which was filtered under suction and washed copiously with water to yield a yellow, crystalline solid. The solid was washed with 150 ml of -10° C. methanol to yield 11.5 g (66%) of white product; mp:127°-129° C.

Provenance & Evidence