Boron trifluoride etherate → 5,5-Dimethyl-3a,4,5,6,7,8,9,9a-octahydronaphtho[2,3-c]furan-1,3-dione

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Reaction Steps

1,2,3,6-tetrahydro-4-(4-methyl-3-pentenyl)phthalic anhydride (VIII, Z=O) (1000g) and boron trifluoride etherate (100 g.) in 1 liter of benzene was refluxed for one and one-half hours. Work-up, using standard techniques, gave in almost quantitative yield crude 1,2,3,4,5,6,7,8-octahydro-5,5-dimethyl-2,3-naphthalenedicarboxylic acid anhydride (VII, X=O; R is the radical C). The cyclized anhydride (1 mole) was heated slowly to 250° C. with 200 ml. of ammonium hydroxide (s.g. 0.91) until ammonia no longer was liberated, using a condenser of a length which allowed ready evaporation of water. The resulting 1,2,3,4,5,6,7,8-octahydro-5,5-dimethyl-2,3-naphthalenedicarboximide (VII, X=NH; R is the radical C) was dissolved in 500 ml. of 2N sodium hydroxide in ethyl alcohol with warming, the solution was evaporated to dryness in vacuo, and the resulting sodium salt of the imide was suspended in 500 ml. of dioxane and treated with trichloromethanesulfenyl chloride (1.1 moles) in 200 ml. of dioxane with gentle stirring. The reaction was completed by heating at 80° C. for thirty minutes. The mixture was allowed to stand overnight, concentrated in vacuo, and the residue was crystallized from ethyl alcohol (or benzene) to give a yield of 91% of the title compound.

Provenance & Evidence