1,4-bis (dihydroxyphenyl) butane and analogs

Details 1,4-bis (dihydroxyphenyl) butane and analogs 1,4-bis (dihydroxyphenyl) butane and analogs

1988-08-19

1990-09-04

Lone, Werren B.

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

Organic compounds

Oxygen containing

568637, 568644, 568646, 568648, 568650, 568717, 568721, 568729, 568808, 568811, C07C 43164, C07C 3912, C07C 3326

Patent

active

049546597

ABSTRACT:
A grignard synthesis of pharmacologically active 1,4-bis(dihydroxyphenyl)butane and analogs, as well as novel intermediates, is provided, comprising preparing a grignard reagent preferably, a 3,4-dialkoxyphenyl propyl magnesium bromide, which may be reacted with carbonyl compounds to form intermediates of desired end products, said carbonyl compounds preferably being 3,4-dialkoxybenzaldehydes. The resulting alcohol is converted to a corresponding ether or siloxy compound, at the carbonyl site. The oxy-substituent is cleaved off; and the benzene ring or rings dealkylated to leave hydroxy substituents on the rings.

REFERENCES:
patent: 3769350 (1973-10-01), Perry
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Ward et al., "Tetrahedron Letters", 32 (1979), 3043-3046.
Fujii et al., Chem. Abs., vol. 83, (1975), 114,160 w.
Ronlan et al., Jour, Org. Chem., 39:7, (1974), 1014-1016.
Ayres et al., Tetrahedron, 25 (1969, 4093-4098.
Gisvold et al., Jour. Amer. Pharm. Assoc., 35 (1946), 188-191.

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