Tricky (Stunning)
07-28-02 03:03
No 338027
      Chloromethylation of ethers of pyrocatechol.  Bookmark   

Through the mixture of 0,1mol of ether of pyrocatechol, 10g of paraform, 3-3,5g of H3PO4, 15-20g of metallic Hg, 200ml of GAA and 40ml of conc. H2SO4 was bubbled stream of HCl during 2,5h at vigorously stirring and 30-45C. After cooling, mixture was poured to 1l of Ice-Water. Falled product was filtered, washed with a little amount of acetic acid till pH=7 and recrystallized from acetone.
NB! In case, if recrystallisation was done from tholuene, the final compounds are 2,3,6,7-tetraalkoxy-9,10-dihydroantratsens
Results of chloromethylations of suitable ethers were:
3,4-dimethoxybenzylchloride M.P.=50-51C, yield is 63%
3,4-diethoxybenzylchloride M.P.=126-127C, yield is 66%
3,4-dipropoxybenzylchloride M.P.=99-101C, yield is 64,5%
3,4-dibutoxybenzylchloride M.P.=86-87C, yield is 74%

Quoted from N. Melnikov and M. Prilutskaja, organicum, pages: 3746-3747

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