Isoprene → 6-Methyl-6-hepten-2-one

Participants

Reaction Steps

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.

Provenance & Evidence