New routes have been developed for the practical syntheses of dl-Muscone(1) employing cyclopentadecanone(2) as the starting material. In this experiment, addition of bromine to cyclopentadecanone in dried E. Ether solution with a trace of $AlCl_3$ as the catalyst were produced 2-bromocyclopentadecanone(3). This process was enhanced formation of regioselective enolate anion at $C_2$ position. 2-Bromocyclopentadecanone was put into $Li_2CO_3$-LiBr-DMF solution at 140��150$^{\circ}C$, were produced trans- and cis-2-cyclopentadecen-1-one(4) mixture. Other by-products were reduced by control of reaction temperature and time. Trans- and cis-2-cyclopentadecen-1-one(4) mixture was directly put into dried E. Ether solvent and induce to react dropwise with $CH_3MgBr-Cu_2Cl_2$ complex, all of them got into 1,4-addition, dl-Muscone (1) was formed as the result. Conculsion, through three steps procedure from cyclopentadecanone(2) to dl-Muscone(1), the pure dl-Muscone was obtained with the high proportion of 85%, and synthetic cost was able to be much lower than any other conventional methods as there were no chemical separating steps.
Citing 'A Newer Short Synthesis of dl-Muscone(Ⅰ)
'
@article{ JCGMDC_1996_v40n4_243}
,title={A Newer Short Synthesis of dl-Muscone(Ⅰ)}
,volume={4}
, number= {4}
, journal={Journal of the Korean Chemical Society}
, publisher={Korean Chemical Society}
, author={D.S., Im
and
D.H., Shin
and
D.K., Park}
, year={1996}
, month={Apr}
TY - JOUR
T2 - Journal of the Korean Chemical Society
AU - D.S., Im
AU - D.H., Shin
AU - D.K., Park
SN - 1017-2548
TI - A Newer Short Synthesis of dl-Muscone(Ⅰ)
VL - 40
PB - Korean Chemical Society
PY - 1996
ER -
D.S., I.
,
D.H., S.
,
&
D.K., P.
( 1996).
A Newer Short Synthesis of dl-Muscone(Ⅰ).
Journal of the Korean Chemical Society,
40
(4)
Korean Chemical Society.
D.S., I
,
D.H., S
,
&
D.K., P
1996,
A Newer Short Synthesis of dl-Muscone(Ⅰ),
Journal of the Korean Chemical Society,
vol. 4,
no. 4,
[1]
I D.S.
,
S D.H.
,
and
P D.K.
,
“A Newer Short Synthesis of dl-Muscone(Ⅰ)”,
Journal of the Korean Chemical Society,
vol. 4,
no. 4,
Apr
1996.
D.S., Im
and
,
D.H., Shin
and
,
D.K., Park
and
,
“A Newer Short Synthesis of dl-Muscone(Ⅰ)”
Journal of the Korean Chemical Society,
4.
4
1996:
D.S., I
,
D.H., S
,
D.K., P
A Newer Short Synthesis of dl-Muscone(Ⅰ).
Journal of the Korean Chemical Society
[Internet].
1996.
Apr ;
4
(4)
D.S., Im
,
D.H., Shin
,
and
D.K., Park
,
“A Newer Short Synthesis of dl-Muscone(Ⅰ).”
Journal of the Korean Chemical Society
4
no.4
()
Apr,
1996):