Author Topic: Chloromethylation of ethers of pyrocatechol.  (Read 1410 times)

0 Members and 1 Guest are viewing this topic.


  • Guest
Chloromethylation of ethers of pyrocatechol.
« on: July 28, 2002, 03:03:00 AM »
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 30-45°C. 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.=50-51°C, yield is 63%
3,4-diethoxybenzylchloride M.P.=126-127°C, yield is 66%
3,4-dipropoxybenzylchloride M.P.=99-101°C, yield is 64,5%
3,4-dibutoxybenzylchloride M.P.=86-87°C, yield is 74%

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

There's a hole in our soul that we fill with dope
And we're feeling fine.