4-Hexen-1-ol, 5-methyl-2-(1-methylethenyl)- → 5-methyl-2-prop-1-en-2-ylhex-4-enal
Reaction equation
C([O:6][CH2:7][C:8](=[C:14]([CH3:16])[CH3:15])[CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])(=O)CCC.C(C(CC=C(C)C)CO)(C)=C.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>>[C:14]([CH:8]([CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])[CH:7]=[O:6])([CH3:16])=[CH2:15]Participants
4
Procedure
Tabata has reported the synthesis of 2-isopropylidene-5-methyl-4-hexenyl butyrate in which 2-isopropenyl-5-methyl-4-hexenol as a starting material is subjected to an oxidation reaction with Dess-Martin reagent to form 2-isopropenyl-5-methyl-4-hexenal (lavandulal), the resulting aldehyde is isomerized under an acidic condition through migration of the double bond to form 2-isopropylidene-5-methyl-4-hexenal (another name: fujikonal), and the isomerized aldehyde is reduced and then esterified to form 2-isopropylidene-5-methyl-4-hexenyl butyrate (Appl. Entomol. Zool., 48, 229-232 (2013)).
Sources & evidence
- ORD record
- ord-18a7de2dc16a4c0a9944eb5c5d29a87f
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09126920B2
Reaction notes
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