Synthesis 2-alkyl cyclopentenolones

Details Synthesis 2-alkyl cyclopentenolones Synthesis 2-alkyl cyclopentenolones

1981-02-12

1982-11-16

Reamer, James H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

568364, 570214, 570215, 549531, C07C 4558, C07C 1730

Patent

active

043595863

ABSTRACT:
2-Hydroxy-3-methylcyclopent-2-en-1-one was synthesized in a five-step synthesis starting from 2-methyl-1,3-butadiene. Novel intermediate steps include the hot tube isomerization of 1,1-dihalo-2-methyl-2-vinylcyclopropane to give 1-methyl-4,4-dihalocyclopent-1-ene, hydrolysis to 3-methyl-2-cyclopenten-1-one, epoxidation of the latter using a phase transfer catalyst, followed by catalyzed isomerization to produce 2-hydroxy-3-methylcyclopent-2-en-1-one in high overall yield.

REFERENCES:
patent: 2833787 (1958-05-01), Carlson et al.
patent: 2951878 (1960-09-01), Neureiter
patent: 2981756 (1961-04-01), Neureiter
patent: 3326842 (1967-06-01), Ketley
patent: 3462453 (1969-08-01), Popoff et al.
patent: 3657348 (1972-04-01), Tobey
patent: 4012430 (1977-03-01), Verbrugge et al.
Keller, "Compendium of Phase Transfer Reactions," (1978).
Ketley et al., J. Org. Chem., vol. 31, pp.305-308, (1966).

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