Science of Synthesis

Pfeiffer, W. D., Science of Synthesis, (2007) 35, 159.

1,3,5-Trioxane is little used for the chloromethylation of arenes. 1-(Chloromethyl)naphthalene can be prepared by reaction of naphthalene with 1,3,5-trioxane–hydrogen chloride in a yield of 63%.[‌38‌] The treatment of 3 equivalents of benzene with 2 equivalents of 1,3,5-trioxane in the presence of zinc(II) chloride in acetic acid with an excess of anhydrous hydrogen chloride affords benzyl chloride in 65% yield.[‌39‌] The reaction of toluene with 1,3,5-trioxane–hydrogen chloride leads to 4-(chloromethyl)toluene (‌11‌) (‌Scheme 7‌).[‌39‌] Ethylbenzene reacts with 1,3,5-trioxane–hydrogen chloride to give 1-(chloromethyl)-4-ethylbenzene.[‌1‌] 1-(Chloromethyl)-4-[4-(chloromethyl)phenyl]benzene is obtained by reaction of 1 mole of biphenyl with 2.2 moles of 1,3,4-trioxane and hydrogen chloride gas.[‌40‌]

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References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8, 8888.