Dimethyl tetradecanedioate

Ring expansion induced by FeCla has been used in a new synthesis of dl-muscone in 237> overall yield from dimethyl tetradecanedioate, which was converted into (6) by the procedure of Ruhimann (4, 537). In this case cyclo-propanation with methylene iodide and diethylzinc (4, 153) proved superior to the Simmons-Smith reagent. ... 

Dimethyl 2,3-bisacetyl-l,14-tetradecanedioate and methyl 2-acetyl-14-oxopentadeconate... 

A mixture of methyl acetoacetate (1 mol), 1,9-decadiene (0.25 mol) and di-t-butyl peroxide (0.1 mol) were heated to 160°C and additional methyl acetoacetate (1.5 mol) added over 2 hours. Thereafter the mixture was stirred one hour at 160°C in order to decompose residue peroxide. Excess methyl acetoacetate was distilled off under reduced pressure and 82g of residue consisting of 57% dimethyl 2,3-bisacetyl-l,14-tetradecanedioate (I) and 4% methyl 2-acetyl-14-oxopentadeconate (II) obtained. The mixture was separated by column chromatography on silica using toluene/acetone, 4 1, and the products isolated. 

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