5-Hexen-1-ol → 84254-20-6
Reaction equation
[Br:1][CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH2:7]Br.BrCCC=CCC.[C:16]([O:19][CH:20]=[CH:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:18])[CH3:17].[CH:26]([OH:32])=[CH:27][CH2:28][CH2:29]CC.[CH2:33]([OH:39])[CH2:34]CCC=C>>[Br:1][CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH3:7].[C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH:25][CH2:29][CH2:28][CH2:27][CH2:26][O:32][C:33](=[O:39])[CH3:34])(=[O:18])[CH3:17].[C:16]([O:19][CH:20]=[CH:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:18])[CH3:17]Participants
8
Procedure
With reference to FIG. 25, olefin metathesis provides, however, an affordable method to produce 8-bromooctan-1-ol. The symmetrical 1,6 dibromo-3-hexene is made by the cross-metathesis of 1-bromo-3-hexene (removing the volatile 3-hexene under vacuum). 1-Bromo-3-hexene is prepared from commercially available leaf alcohol (Bedoukian, Danbury Conn.) that sells for approximately $50 U.S./Kg, and 1,10-diacetoxy-5-decene is prepared by the cross-metathesis of hexenyl acetate. Hexenyl acetate is prepared from hexenol by conventional methods. 5-Hexenol sells for approximately $50 U.S./Kg and is available from Degussa-Huls, Somerset, N.J.
Workup
- customremoving the volatile 3-hexene under vacuum)
Sources & evidence
- ORD record
- ord-bb3d8bec5c64456e934a6d6289940a5f
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06696597B2
Reaction notes
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