Bicyclic aldehydes

Details Bicyclic aldehydes Bicyclic aldehydes

1978-04-20

1980-04-08

Helfin, Bernard

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

Organic compounds

Carboxylic acid esters

568820, 260648R, 260601H, 260598, 2604105, C07C 4734, C07C 4744, C07C 6902

Patent

active

041974115

ABSTRACT:
2-Halomethyl-, 2-alkoxymethyl- and 2-acyloxymethyl-3-methyl-3-formyl-bicyclo[2.2.1]heptane and -hept-5-ene and a process for their preparation.
The new compounds are obtained by reacting cyclopentadiene or dicyclopentadiene with the corresponding 4-halo-, 4-alkoxy- or 4-acyloxy-2-methyl-crotonaldehydes under the conventional conditions for Diels-Alder reactions, with or without subsequent catalytic hydrogenation of the Diels-Alder adduct obtained. The new compounds provide an industrially easily realized and advantageous method of synthesis of the sought-after essential ingredients of natural sandalwood oils.

REFERENCES:
patent: 3067244 (1962-12-01), Robinson et al.
Brieger, Tetrahedron Letters, No. 28 (1963) 1949-1951.
Ohloff, "Fortschritte der Chemischen Forschung" 12 (1969) 212-215.
Saver, Angewandte Chemie, 79 (1967) 76-94.
Duttmann et al., Ann. Chem. (1976) 1753-1756.

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