14-oxobicyclo(10.4.0)hexadec-1(12)-ene,...

Details 14-oxobicyclo(10.4.0)hexadec-1(12)-ene,... 14-oxobicyclo(10.4.0)hexadec-1(12)-ene,...

C - Chemistry, Metallurgy

07

C

167/321, 260/581

C07C 49/385 (2006.01) C07C 49/613 (2006.01) C11B 9/00 (2006.01)

Patent

CA 1048058

ABSTRACT 14-Oxobicyclo [10.4.0] hexadec-1 (12)-ene (I) which has an extremely strong, sweet musk odor and is useful in the perfume art as an odorant, is prepared by reaction of cyclododecane with morpholine to produce 1-morpholinocyclodo- decene, reaction of this product with methyl vinyl ketone followed by acid hydrolysis to form 2-(3-oxobutyl) cyclodo- decanone, and base-catalyzed cyclization of this diketone to a mixture of (I) and its isomer 14-oxobicyclo[10.4.0] hexadec- 12-ene (II) containing less than about 10% of (I). A product enriched in (I)is obtained by distillation of this mixture in the presence of base, or by ketallization of (I) and (II) followed by hydrolysis. Hydrogenation of (I) or (II) or hydrogenation of their ketals followed by hydrolysis yields 14-oxobicyclo[10.4.0] hexadecane, which has a musky odor and, like (I) is useful as an odorant.

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