8-(2-Chlorophenylmethylene)-1,4-dioxaspiro[4.5]decane → 8-(2-Chlorophenylmethyl)-1,4-dioxaspiro[4.5]decane

Participants

Reaction Steps

A solution of 6.9 grams (0.026 mole) of 8-(2-chlorophenylmethylene)-1,4-dioxaspiro[4.5]decane in about 50 mL of ethanol and 0.4 gram (catalyst) of 10% palladium on charcoal were placed in a hydrogenation bottle and hydrogenated using a Parr hydrogenation apparatus. Upon the theoretical uptake of hydrogen, the reaction mixture was filtered to remove the catalyst. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography using silica gel. Elution was accomplished using 33% ethyl acetate in hexane. The product-containing fractions were combined and concentrated under reduced pressure, yielding 5.0 grams of 8-(2-chlorophenylmethyl)-1,4-dioxaspiro[4.5]decane. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence