SYNTHESIS: A solution of
1,4-dimethoxy-5,6,7,8-tetrahydro-beta-naphthaldehyde (see preparation
under 2C-G-4) in 20 mL nitroethane was treated with 0.13 g anhydrous
ammonium acetate and heated on the steam bath overnight. The
volatiles were removed under vacuum and the residue, on cooling,
spontaneously crystallized. This crude rust-colored product (1.98 g)
was recrystallized from 15 mL boiling MeOH yielding, after filtering
and air drying to constant weight, 1.33 g of
1-(2,5-dimethoxy-3,4-(tetramethylene)phenyl)-2-nitropropene as dull
gold-colored crystals. The mp was 94-94.5 °C. Anal. (C15H19NO4) C,H.
DOSAGE: unknown.
DURATION: unknown.
EXTENSIONS AND COMMENTARY: The discussion that appeared in the
commentary section under 2C-G-4 applies here as well. The major
struggles were in the preparation of the aldehyde itself. And
although the final product has not yet been made, this last synthetic
step should be, as Bobby Fischer once said in his analysis of a
master's chess game following a blunder by his opponent, simply a
matter of technique.
As with the phenethylamine counterpart, G-4 has a structure that lies
intermediate between G-3 and G-5, both potent compounds. It is
axiomatic that it too will be a potent thing, and all that now needs
be done is to complete its synthesis and taste it.
Back]
]