1-Bromo-3-chloropropane → (Z,Z,E)-1,1-diethoxy-7,11,13-hexadecatriene
Reaction equation
Cl[CH2:2][CH2:3]CCC/C=C\CC/C=C\C=C\CC.[CH2:17]([OH:29])[CH2:18]/C=C\CC/C=C\C=C\CC.ClCC/C=C\CC/C=C\C=C\CC.BrCCCCl.[CH:48](=[O:64])[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53]/[CH:54]=[CH:55]\[CH2:56][CH2:57]/[CH:58]=[CH:59]\[CH:60]=[CH:61]\[CH2:62][CH3:63].C([O-])([O-])OCC>>[CH2:2]([O:64][CH:48]([O:29][CH2:17][CH3:18])[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53]/[CH:54]=[CH:55]\[CH2:56][CH2:57]/[CH:58]=[CH:59]\[CH:60]=[CH:61]\[CH2:62][CH3:63])[CH3:3]Participants
Procedure
In one aspect of the invention, there is provided (Z,Z,E)-1-chloro-6,10,12-pentadecatriene. In another aspect of the invention, there is also provided a method for preparing (Z,Z,E)-1-chloro-6,10,12-pentadecatriene comprising a step of chlorinating (Z,Z,E)-3,7,9-dodecatrien-1-ol into (Z,Z,E)-1-chloro-3,7,9-dodecatriene and a step of reacting a Grignard reagent into which the (Z,Z,E)-1-chloro-3,7,9-dodecatriene is converted with 1-bromo-3-chloropropane. In a further aspect of the invention, there is also provided a method for preparing (Z,Z,E)-7,11,13-hexadecatrienal comprising a step of reacting a Grignard reagent into which (Z,Z,E)-1-chloro-6,10,12-pentadecatriene is converted with ethyl orthoformate to obtain (Z,Z,E)-1,1-diethoxy-7,11,13-hexadecatriene, and a step of treating the (Z,Z,E)-1,1-diethoxy-7,11,13-hexadecatriene with an acid to obtain (Z,Z,E)-7,11,13-hexadecatrienal.
Workup
- customIn another aspect of the invention, there is also provided a method
- customIn a further aspect of the invention, there is also provided a method
Sources & evidence
- ORD record
- ord-8ddc605a43cf463c8d6ff70afede25ae
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829255B1
Reaction notes
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