Isoprene → 6-Methyl-6-hepten-2-one
Reaction equation
P(Cl)(Cl)Cl.P(Br)(Br)Br.C(OCC)(=O)[CH2:10][C:11]([CH3:13])=[O:12].[CH2:18]=[CH:19][C:20](=[CH2:22])[CH3:21]>>[CH3:22][C:20](=[CH2:21])[CH2:19][CH2:18][CH2:10][C:11](=[O:12])[CH3:13]Participants
5
Procedure
3,7,11-trimethyldodeca-1-yne-6,11-dien-3-ol can be obtained by halogenating 3-methyl-3-buten-1-ol, which is formed as a by-product in isoprene synthesis with phosphorus trichloride or phosphorus tribromide, reacting the halogenation product with ethyl acetoacetate to form 6-methyl-6-hepten-2-one, subjecting 6-methyl-6-hepten-2-one to ethynylation in the same manner as described above, thereafter subjecting the ethynylation product to partial hydrogenation in the presence of a Lindler catalyst, subjecting the partial hydrogenation product to Caroll rearrangement by using ethyl acetoacetate or diketene, and subjecting the rearrangement product to ethynylation.
Sources & evidence
- ORD record
- ord-1d878140c0e34ddd966cd2392d93d6e9
- Source dataset
- uspto-grants-1976_08
- Patent number
- US03975451
Reaction notes
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