Process for producing dihydronaphthalene derivatives

Details Process for producing dihydronaphthalene derivatives Process for producing dihydronaphthalene derivatives

1982-03-29

1983-11-29

Helfin, Bernard

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

Organic compounds

Oxygen containing

C07C 4118

Patent

active

044182180

ABSTRACT:
2-(1'-hydroxy)ethyl-5,8-dimethoxy-3,4-dihydronaphthalene of the formula ##STR1## is produced by reducing 2-acetyl-5,8-dimethoxy-3,4-dihydronaphthalene of the formula, ##STR2## with a reducing agent obtained by reacting one equivalent of lithium aluminum hydride with one equivalent of an optically active N-substituted ephedrine of the formula, ##STR3## (wherein R.sub.1 is a C.sub.1 -C.sub.4 alkyl group or benzyl group, and Ph is phenyl group) and two equivalents of an N-substituted aniline of the formula, ##STR4## (wherein R.sub.2 is a C.sub.1 -C.sub.4 alkyl group or phenyl group, and Ph is phenyl group).

REFERENCES:
patent: 4316985 (1982-02-01), Broadhurst et al.
Tetrahedron Letters, No. 24, 2065-2068 (1974).
Tetrahedron, vol. 32, 939-944 (1976).
Tetrahedron Letters, No. 29, 2683-2686 (1979).
Tetrahedron Letters, vol. 21, 1735-1738 (1980).
J. Am. Chem. Soc., vol. 101, 3129-3131, 5843-5844, (1979).
Asami et al, Heterocycles, vol. 12, No. 4 (1979) 499-502.
Shimba et al, Chemistry Letters (1979) 783-784.
Asami et al, Bull. Chem. Soc. Japan, vol. 51 (1978) 1869-1873.

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