Process for synthesizing heliotropine and its derivatives

Details Process for synthesizing heliotropine and its derivatives Process for synthesizing heliotropine and its derivatives

2004-10-28

2008-07-22

Witherspoon, Sikarl A (Department: 1621)

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

Organic compounds

Oxygen containing

C568S437000

Reexamination Certificate

active

07402709

ABSTRACT:
A new high-yield, easily industrialized process for synthesizing compounds of formula (IV), in which X1and X2, the same or different, are linear or branched C1-C8 alkyls, n and m are 0, 1 or 2, with the proviso that n and m are not simultaneously 0; or (OX1)n and (OX2)m taken together form an O-T-O group where T is chosen from —CH2—, —CH2CH2, —CH2CH2CH2—, —C(CH3)2—. The process comprises treating a chloromethyl derivative (I) with an alkaline acetate to form the intermediate acetylderivative (II); the intermediate (II) is to hydrolysed to form the alcohol (III); the alcohol (III) is then oxidised in the presence of air and catalysts to obtain the desired derivative (IV). The process runs its course within a short period of time, with high yields and high selectivity; in addition, the process does not require purification and separation of the intermediates and can therefore be favourably conducted in a single batch.

REFERENCES:
patent: 5095128 (1992-03-01), Sidot et al.
patent: 55022615 (1980-02-01), None
patent: 57009734 (1982-01-01), None
Quelet et al., “Synthesis of Anisic Alcohol”,Database Caplus, Chemical Abstracts Service, No. 1937:817 Columbus, Ohio (1937).
Futami et al., “Reactions of Alkylarenes, Benzyl Alcohols, Sulfides, and Phosphine with Manganese (III) Acetate-Chloride Ions”,Bulletin of the Chemical Society of Japan, vol. 62, No. 11, pp. 3567-3571 (1989).

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