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.
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.
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