Optically active nordihydroguaiaretic acid and intermediates

Details Optically active nordihydroguaiaretic acid and intermediates Optically active nordihydroguaiaretic acid and intermediates

1982-10-25

1985-12-31

Helfin, Bernard

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

Organic compounds

Oxygen containing

568636, 568646, 568729, 556482, C07C 43205, C07C 43263, C07C 3916

Patent

active

045622981

ABSTRACT:
A process for producing novel compositions including optically active molecules of nordihydroguaiaretic acid (d,1-2,3-dimethyl,1,4-bis(3,4-dihydroxyphenyl)butane) and intermediates, starting with 1,4-bis(3,4-dimethoxyphenyl)butanone, or other structurally similar composition having oxy substituents at the 3,4-phenyl positions, comprising (1) forming the corresponding butanol; (20) forming the corresponding 1,4-butane ether or siloxy composition; (3) cleaving the oxy substituent from the butane chain at the 1 and 4 positions; (4) dealkylating the phenols at the 3,4 positions to leave hydroxy substituents with hydrobromic acid reflux for 8 to 10 hours. Optical orientation is preserved throughout.

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Schrecker et al., J.A.C.S., 77, (1955), 432-437.
Gisvold et al., J. Amer. Pharm. Assoc., 35 (1946), 188-191.

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