Manufacture of 2-(alkyl, alkenyl or alkynyl) 3-carbalkoxyalkyl k

Details Manufacture of 2-(alkyl, alkenyl or alkynyl) 3-carbalkoxyalkyl k Manufacture of 2-(alkyl, alkenyl or alkynyl) 3-carbalkoxyalkyl k

1976-10-28

1979-03-06

Gerstl, Robert

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

Organic compounds

Carboxylic acids and salts thereof

260586R, 260586C, 560122, C07C 5134

Patent

active

041432304

ABSTRACT:
The copper enolate of 3-allylcyclopentanone is alkylated with an alkyne so as to form the 2-alkynyl, 3-allylcyclopentanone which is then subjected to ozonolysis and oxidative cleavage to form 2-alkynylcyclopentan-3-one-1-yl alkylcarboxlic acid. The acid can be esterified to form a 2-alkynyl-3-carbalkoxyalkyl ketone which, in turn, can be hydrogenated to convert the alkynyl moiety to alkenyl or alkyl moieties. The procedure is particularly useful in the synthesis of methyl dl-jasmonate, dehydrojasminate and dihydrojasmonate.

REFERENCES:
patent: 3754016 (1973-08-01), Oberhansli

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