Thanks moo!
I did a quick literature search for 4-methoxy-3,5-dimethylphenol but didn't came up with anything..
This could be an alternative approach, although allyltributyl stannate is pretty expensive (20 euro/gram):
Reactants: 2,6-dimethyl-[1,4]benzoquinone and allyl-tributyl-stannane
Product: 2-allyl-3,5-dimethylhydroquinone
Yield: 82 percent
Reagent: BF3*OEt2
Solvent: CH2Cl2
Temperature: -78 C
Naruta, Yoshinori; J.Amer.Chem.Soc.; EN; 102; 11 (1980) 3774-3783.
http://pubs.acs.org/cgi-bin/sample.cgi/jacsat/1980/102/i11/pdf/ja00531a019.pdf
Methylation will give 2,5-dimethoxy-4,6-dimethyl-allylbenzene.
Mmm, this is probably a better way:
2-allyl-3,5-dimethylphenol is prepared by Claisen rearrangement of allyl-(3,5-dimethylphenyl)-ether using either:
* allyl bromide: Wehrli,R. et al.; Helv.Chim.Acta 60 (1977) 2034-2061.
* allyl chloride: Le Noble,W.J. et al.; J.Org.Chem. 36 (1971) 193-196.
http://pubs.acs.org/cgi-bin/sample.cgi/joceah/1971/36/i01/pdf/jo00800a039.pdf
EDIT: The title of the article starts with "Chemical reactions under high pressure", so I guess we better scratch this one.Next, 2-allyl-3,5-dimethyl-1,4-benzoquinone is prepared from 2-allyl-3,5-dimethylphenol by oxidation with O
2 and Co(II) salts according to:
Matsumoto, Masakatsu; Watanabe, Nobuko; Mori, Eiko; Aoyama, Misao; Kusunoki, Jun and Yamaura, Tetsuaki;
Heterocycles 38; 12 (1994) 2589-2592.
This paper also describes the reduction of the benzoquinone to 2-allyl-3,5-dimethylhydroquinone using NaBH
4.