Shame on you bees! Let's get busy and find the necessary refs to save this thread from becoming a farce!
Ok, this being said here is my contribution:
1,2,3-trimethoxybenzene ------> 1,3-dimethoxybenzene
Look at what Ugo Azzena et. al. have to say about it:
Synthesis 1; 1989; 28-30; / K, THF, RT, 24 hrs, 86%!
Tetrahedron Lett. 30; 13; 1989; 1689-90; / K, THF, RT, 24hrs
J. Org. Chem. 55; 19; 1990; 5386-5390; / K, THF, RT, 24hrs
Some other refs useful for this reaction:
J. Chem. Soc. Chem. Commun.; 1987; 1549-50 / K, THF, 87%, olivetol dimethyl ether also included, the one that started it all
J. Org. Chem. 57; 11; 1992; 3101-3106 Good one read it!
Chem. Ber. 44; 1911; 2135; / Na, EtOH; 1,2,3-trimethoxybenzene reduction
Synthesis 1990; 313-14;
1.) trimethoxybenzaldehyde dimethylacetal ---> 4-butyl-3,5-diMeO-benzaldehyde; Na, THF, RT, 53hrs, 86%!!!!
2.) trimethoxybenzaldehyde dimethylacetal ---> 4-ethyl-3,5-diMeO-benzaldehyde; Na, THF, 53hrs, RT, 75%
3.) trimethoxybenzaldehyde dimethylacetal ---> 3,5-dimethoxybenzaldehyde; Na, THF, 53hrs, RT, 92%
Recl. Trav. Chim. Pay-Bas, 109, 7/8; 1990, 443-445; / trimethoxybenzene ---> 1,3-dimethoxy-2-butylbenzene; BuLi, hexane
J. Org. Chem. 55; 19; 1990; 5386-5390; / trimethoxybenzene ---> (2,6-dimethoxyphenyl)trimethylsilane; 1) K, THF, RT, 24hrs; 2) THF, -50°C, 6hrs, chlorotrimethylsilane
Silicon containing psychedelics! We are the borgs and you will all be assimilated
Lots of useful shit in here (other metals, other electrophiles, substrates, regioselectivity, temp. dependence, product distributions). Get it and read it!
Chem. Ber. 41; 1908; 2556; / Na; EtOH; 5-allyl-1,2,3-trimethoxybenzene ---> 1,3-dimethoxy-5-propylbenzene
J. Chem. Soc. Perkin Trans 1; 3; 1995; 261-266
Tertrahedron Lett. 34; 35; 1993; 5635-38
And the special gift, ready for your favorite trifluoromethylation:1,2,3-trimethoxybenzene -----> 2-iodo-1,3-dimethoxybenzene:
you guessed right, it another one of those Ugo Azzena refs listed above, the JOC 55 one.
1)K, THF, RT, 24hrs,
2) THF, -30°C, 2h, I2
Same works with bromine @ -78°C