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classificationCPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D313-00
classificationIPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D313-00
filingDate 1972-11-29-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 1975-01-14-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_10cdb6775b650ef66c0ec12ac2f1cf74
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_1e9b0440fe4bac8eb16e9c6dedcd0d07
publicationDate 1975-01-14-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber US-3860616-A
titleOfInvention Synthesis of d,1-zearalanol
abstract The preparation of d,1-zearalanol and mono- and di-ethers thereof, compounds exhibiting anabolic, estrogenic and fertility control properties, are prepared from readily available chemical intermediates. Catalytic reduction of the aliphatic double bond and the carbonyl moiety of 2-(10''-hydroxy-6''-oxo-1''-trans undecenyl)-4,6-dimethoxy benzoic acid affords a tetrahydro seco acid which is ring closed with trifluoroacetic anhdyride to yield d,1-zearalanol-2,4-dimethylether; cleavage of the diether is accomplished with boron tribromide to produce d,1-zearalanol. Alternatively, catalytic reduction of the aliphatic double bond of 2-(10''-hydroxy-6''-oxo-1''-trans undecenyl)-4,6-dimethoxy benzoic acid produces a dihydro seco acid which is ring closed with trifluoroacetic anhydride to yield d,1-zearalanone-2,4dimethyl ether; reduction of the carbonyl function affords d,1zearalanol-2,4-dimethyl ether which is reacted with boron tribromide to produce d,1-zearalanol.
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