Method for producing rosefuran precursor and intermediates there

Details Method for producing rosefuran precursor and intermediates there Method for producing rosefuran precursor and intermediates there

1996-03-11

1997-05-06

Reamer, James H.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

560174, 562577, C07D30788

Patent

active

056272880

ABSTRACT:
Disclosed are 3,7-dimethyl-4-oxo-7-octenoic acid and its alkyl esters which are intermediates for producing a fragrance, rosefuran and which are represented by: ##STR1## where R is H or a lower alkyl. The compounds [1] are obtained by reacting 2-methyl-3-alkoxycarbonylpropionic acid halide and 3-methyl-3-butenylmagnesium halide. The octenoic acid [1] is treated with acetic anhydride under heat in the presence of an acidic catalyst to give 3,7-dimethyl-2,6-octadien-4-olide. The olide is reduced in an ordinary manner to give rosefuran.

REFERENCES:
patent: 3819733 (1974-06-01), Ramsden
patent: 4853473 (1989-08-01), Fischer et al.
Tetrahedron Letters No. 50, pp. 4443-4446, 1977. "Prenylations of But-2-Enolides: Synthesis of Rosefuran and Related Natural Furans", David R. Gedge and Gerald Pattendam.
Chemistry Letters, pp. 1791-1794, 1983. "Highly Chemoselective Synthesis of Ketones From Carboxylic Acids and . . . " Tamotsu Fujisawa et al.

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